Cyclopropanecarbonyl chloride → 5-Cyclopropylcarbonylamino-3-isopropylisothiazole-4-carbonitrile

HRID 1735686Notes

Reaction equation

HRID 1735686 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[NH2:7][C:8]1[S:12][N:11]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:9]=1[C:16]#[N:17]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH:1]1([C:4]([NH:7][C:8]2[S:12][N:11]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:9]=2[C:16]#[N:17])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 152801535-Amino-3-isopropylisothiazole-4-carbonitrile

Product 1

HCID 152801545-Cyclopropylcarbonylamino-3-isopropylisothiazole-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×

Procedure

12.5 g of cyclopropanecarbonyl chloride in 30 ml of toluene are added dropwise to a solution of 16.7 g of 5-amino-4-cyano-3-isopropylisothiazole and about 0.5 g of DMAP (N,N-dimethylaminopyridine) in 200 ml of toluene and 200 ml of pyridine. The solution is stirred for 16 hours at room temperature and then evaporated to dryness, and the residue is taken up in ethyl acetate. The organic phase is extracted with aqueous sodium bicarbonate solution and 10% strength hydrochloric acid and is dried and evaporated down.

Workup

  1. customevaporated to dryness
  2. extractionThe organic phase is extracted with aqueous sodium bicarbonate solution and 10% strength hydrochloric acid
  3. customis dried
  4. customevaporated down

Sources & evidence

ORD record
ord-143848ac62f74fd2acd8cf73b494c02a
Source dataset
uspto-grants-1996_07
Patent number
US05538939

Reaction notes

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