Pentane → HCID 67079770, compound

HRID 2194333Notes

Reaction equation

HRID 2194333 reaction equation
[Cl:1][C:2]1([C:5]2OC(=O)[S:7][N:6]=2)[CH2:4][CH2:3]1.[S:11]([C:21]#[N:22])([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].CCCCC>ClC1C=CC=CC=1Cl>[Cl:1][C:2]1([C:5]2[N:22]=[C:21]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[S:7][N:6]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8003PentaneHCID 87946p-Toluenesulphonyl cyanideHCID 67079223HCID 67079223, compound

Product 1

HCID 67079770HCID 67079770, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

66.2 g (372 mmol) of 5-(1-chlorocyclopropyl)-1,3,4-oxathiazol-2-one and 70.9 g (391 mmol) of tosyl cyanide are stirred in 125 ml of 1,2-dichlorobenzene at 160° C. for 1 h. Subsequently, the reaction mixture is cooled and treated with pentane, and the precipitate is filtered off and dried under vacuum. 100.0 g of product are obtained (99.9% purity, 85.2% yield, log P (pH 2.3)=3.67).

Workup

  1. temperatureSubsequently, the reaction mixture is cooled
  2. filtrationthe precipitate is filtered off
  3. customdried under vacuum

Sources & evidence

ORD record
ord-11b146b7e5b34db3bd34b40fe8ed7e40
Source dataset
uspto-grants-2012_12
Patent number
US08334235B2

Reaction notes

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