Acetyl chloride → HCID 23458504, compound

HRID 1679927Notes

Reaction equation

HRID 1679927 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]3[CH:11]([C:12](=[O:15])[NH:13][N:14]=2)[CH2:10]3)[CH:5]=[CH:6][CH:7]=1.[C:16](Cl)(=[O:18])[CH3:17]>C1(C)C=CC=CC=1>[C:16]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]3[CH:11]([C:12](=[O:15])[NH:13][N:14]=2)[CH2:10]3)[CH:5]=[CH:6][CH:7]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 23458522HCID 23458522, compound

Product 1

HCID 23458504HCID 23458504, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.0 g (29.8 millimoles) of 2-(m-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one (see Example 33), 3.5 g (44.6 millimoles) of acetyl chloride and 100 ml of anhydrous toluene are kept at 80° C. for 6 hours. The product is filtered off at 10° C., washed first with toluene and then with water, and recrystallized from methanol. 2.9 g (40% of theory) of 2-(m-acetylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one are obtained as almost colorless crystals, of melting point 200°-202° C.

Workup

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

Sources & evidence

ORD record
ord-c5417c269bf14e5b82f9a2d844383c89
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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