Cyclopropanecarbonyl chloride, 1-chloro- → 2-[p-(1-Chlorocyclopropylcarbonylamino)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one

HRID 1679934Notes

Reaction equation

HRID 1679934 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]3[CH:11]([C:12](=[O:15])[NH:13][N:14]=2)[CH2:10]3)=[CH:4][CH:3]=1.[Cl:16][C:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1>O1CCCC1>[Cl:16][C:17]1([C:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:9]4[CH:11]([C:12](=[O:15])[NH:13][N:14]=3)[CH2:10]4)=[CH:6][CH:7]=2)=[O:21])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 10942508Cyclopropanecarbonyl chloride, 1-chloro-HCID 202648445-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one

Product 1

HCID 234584832-[p-(1-Chlorocyclopropylcarbonylamino)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-oneYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g (24.8 millimoles) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one, 4.5 g (32.4 millimoles) of 1-chlorocyclopropanecarboxylic acid chloride and 100 ml of absolute tetrahydrofuran are kept at room temperature for 6 hours. The product is filtered off at 10° C., washed first with tetrahydrofuran and then with water, and recrystallized from methanol. 4.7 g (62% of theory) of 2-[p-(1-chlorocyclopropylcarbonylamino)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one are isolated as colorless crystals, of melting point 221°-222° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed first with tetrahydrofuran
  3. customwith water, and recrystallized from methanol

Sources & evidence

ORD record
ord-726c4ad081414f01a2019d784664eacc
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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