Water → 53676-36-1

HRID 36872Notes

Reaction equation

HRID 36872 reaction equation
ClS([N:5]=C=O)(=O)=O.[C@@H:8]1([C:14]([O:16][CH3:17])=[O:15])[CH2:10][C@@H:9]1[C:11](O)=O.CN(C=O)C.O>C1C=CC=CC=1>[C:11]([C@H:9]1[CH2:10][C@H:8]1[C:14]([O:16][CH3:17])=[O:15])#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 109756001-Methyl (1R,2S)-1,2-cyclopropanedicarboxylate

Product 1

HCID 5369632553676-36-1Yield 55.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

In 25 ml of benzene was dissolved 13.77 g (97 mmol) of chlorosulfonyl isocyanate, and to the solution was added 12.7 g (88 mmol) of cis-methyl hydrogen cyclopropane-1,2-dicarboxylate which had been synthesized by the process of Journal of Organic Chemistry, Vol. 36, pp. 3356-3361 (1971). The mixture was stirred on an oil bath at 60° C. for 30 minutes. After cooling, 13.6 ml (176 mmol) of DMF was added thereto, followed by stirring for 30 minutes. Water was added thereto, and the reaction mixture was extracted with benzene. The organic layer was washed successively with water and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was distilled under reduced pressure to obtain 6.14 g (55.7%) of methyl cis-2-cyanocyclopropanecarboxylate.

Workup

  1. customhad been synthesized by the process of Journal of Organic Chemistry, Vol. 36
  2. temperatureAfter cooling
  3. stirringby stirring for 30 minutes
  4. extractionthe reaction mixture was extracted with benzene
  5. washThe organic layer was washed successively with water
  6. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-79d4180a5ba0421ea6aa02959fa4c2e2
Source dataset
uspto-grants-1995_05
Patent number
US05418232

Reaction notes

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