IP Library Granted Patent US 9,815,781
Granted Patent B1
US 9,815,781 · App. 15/045,447 · Granted Nov 14, 2017

Process for preparing 3-(methylsulfonyl)propionitrile

Inventors: Gerald S. Jones (Norwood, MA); Scott A. Goodrich (Stoughton, MA)
Assignee: OLATEC THERAPEUTICS LLC
C07C315/02C07C315/06C07C319/06
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Quick Facts
Patent No.
US 9,815,781
App. No.
15/045,447
Granted
Nov 14, 2017
Kind
B1
Abstract

The present invention relates to processes for preparing for preparing 3-(methylsulfonyl)propionitrile. The processes comprise the steps of first reacting 2-chloroethyl methyl sulfide with sodium cyanide or potassium cyanide in a solvent or a solvent mixture to form 3-(methylthio)propionitrile, and then reacting the isolated 3-(methylthio)propionitrile with acetic anhydride, acetic acid, and hydrogen peroxide to form 3-(methylsulfonyl)propionitrile.

Claims (15)

1. A method for preparing 3-(methylsulfonyl)propionitrile, comprising the steps of:

(a) mixing and reacting 2-chloroethyl methyl sulfide with sodium cyanide or potassium cyanide in a solvent mixture of water and a water-immiscible organic solvent at 20-100° C.,

(b) allowing the reaction mixture of (a) to settle and to separate into an aqueous phase and an organic phase,

(c) isolating 3-(methylthio)propionitrile in the organic phase,

(d) mixing the isolated 3-(methylthio)propionitrile with acetic anhydride, acetic acid, and hydrogen peroxide at 25-42° C. to form 3-(methylsulfonyl)propionitrile, and

(e) isolating 3-(methylsulfonyl)propionitrile from the reaction mixture of (d).

2. A method for preparing 3-(methylsulfonyl)propionitrile, comprising the steps of:

(a) mixing and reacting 2-chloroethyl methyl sulfide with sodium cyanide or potassium cyanide in a solvent mixture of water and a water-immiscible organic solvent at 20-100° C.,

(b) allowing the reaction mixture of (a) to settle and to separate into an aqueous phase and an organic phase,

(c) isolating 3-(methylthio)propionitrile in the organic phase,

(d) mixing the isolated 3-(methylthio)propionitrile with acetic anhydride,

(e) reacting the mixture of (ii) with an aqueous solution comprising acetic acid, acetic anhydride and hydrogen peroxide at 25-42° C. to form 3-(methylsulfonyl)propionitrile, and

(f) isolating 3-(methylsulfonyl)propionitrile from the reaction mixture of (e).

3. The method of claim 1 , wherein the water-immiscible organic solvent is ethyl acetate or diethyl ether.

4. The method of claim 2 , wherein the water-immiscible organic solvent is ethyl acetate or diethyl ether.

Assignments (2)
CHANGE OF NAME Recorded Nov 7, 2023
From: OLATEC THERAPEUTICS LLC
To: OLATEC THERAPEUTICS, INC.
Reel/Frame 065489/0809 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2016
From: JONES, GERALD S.; GOODRICH, SCOTT A.
To: OLATEC THERAPEUTICS LLC
Reel/Frame 037803/0610 →
Continuity (1)
Provisional Application 62118035 · Feb 20, 2015