Pentane → HCID 67080890, compound

HRID 389834Notes

Reaction equation

HRID 389834 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3OC(=O)[S:13][N:12]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[S:17]([C:27]#[N:28])([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18].CCCCC>ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]3[N:28]=[C:27]([S:17]([C:20]4[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=4)(=[O:19])=[O:18])[S:13][N:12]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8003PentaneHCID 87946p-Toluenesulphonyl cyanideHCID 672348475-[1-(4-Chlorophenyl)cyclopropyl]-1,3,4-oxathiazol-2-one

Product 1

HCID 67080890HCID 67080890, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

5.00 g (19.71 mmol) of 5-[1-(4-chlorophenyl)cyclopropyl]-1,3,4-oxathiazol-2-one and 3.75 g (20.69 mmol) of tosyl cyanide are stirred in 14 ml of 1,2-dichlorobenzene at 160° C. for 1 h. Subsequently, the reaction mixture is cooled, 10 ml of pentane are added and the precipitate is filtered off and dried under vacuum. 6.43 g of product are obtained (86.7% purity, 72.3% yield; log P (pH2.3)=4.97).

Workup

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

Sources & evidence

ORD record
ord-5143f2d42a6b42d08af9719c783ce270
Source dataset
uspto-grants-2013_02
Patent number
US08383139B2

Reaction notes

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