2,2-Difluoroacetyl chloride → HCID 70571914, compound

HRID 1679932Notes

Reaction equation

HRID 1679932 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.[F:16][CH:17]([F:21])[C:18](Cl)=[O:19]>O1CCCC1>[OH2:15].[F:16][CH:17]([F:21])[C:18]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]3[CH:11]([C:12](=[O:15])[NH:13][N:14]=2)[CH2:10]3)=[CH:6][CH:7]=1)=[O:19].[F:16][CH:17]([F:21])[C:18]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]3[CH:11]([C:12](=[O:15])[NH:13][N:14]=2)[CH2:10]3)=[CH:6][CH:7]=1)=[O:19]

Participants

4

Reactant 2

HCID 27368902,2-Difluoroacetyl chlorideHCID 202648445-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one

Product 1

HCID 70571914HCID 70571914, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.0 g (14.9 millimoles) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one, 2.0 g (17.5 millimoles) of difluoroacetyl chloride and 100 ml of absolute tetrahydrofuran are kept first for 3 hours at 0°-5° C. and then for 20 hours at room temperature. The product is filtered off at 10° C., washed with water and recrystallized from methanol. 2.7 g (63% of theory) of 2-(p-difluoroacetylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one hemihydrate are obtained as colorless crystals, of melting point 223°-224° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed with water
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e205c6d4a8494903ba3e81ad1877a1ba
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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