Water → HCID 23458481, compound

HRID 1679919Notes

Reaction equation

HRID 1679919 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.[C:16](Cl)(=[O:19])[CH:17]=[CH2:18].O>C1(C)C=CC=CC=1>[C:16]([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])[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 962WaterHCID 13140Acryloyl chlorideHCID 202648445-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one

Product 1

HCID 23458481HCID 23458481, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using a method similar to Example 11, 6.0 g (29.8 millimoles) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one (see Example 8a) are reacted with 4.05 g (44.7 millimoles) of acryloyl chloride in toluene. The product is filtered off at 10° C., washed first with toluene and then with water, and recrystallized from a dimethylformamide/water mixture. 3.5 g (45% of theory) of 2-(p-acryloylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one, hydrated with one mole of water per four moles of compound, are isolated as almost colorless crystals of melting point 240°-241° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed first with toluene
  3. customwith water, and recrystallized from a dimethylformamide/water mixture

Sources & evidence

ORD record
ord-c979c93692e64c29833743fab8e6c81e
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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