Water → HCID 23458562, compound

HRID 1679918Notes

Reaction equation

HRID 1679918 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])[CH2:17][CH3:18].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])[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 62324Propionyl chlorideHCID 202648445-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one

Product 1

HCID 23458562HCID 23458562, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.0 g (29.8 millimoles) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one (see Example 9b), 4.2 g (45.4 millimoles) of propionyl chloride and 100 ml of anhydrous toluene are kept at 80° C. for 6 hours. The product is then filtered off at 10° C., washed first with toluene and then with water, and dried under reduced pressure at 50° C. 6.5 g (83% of theory) of 2-(p-propionylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one, hydrated with one mole of water per four moles of compound, are obtained as almost colorless crystals, of melting point 252°-253° C. after recrystallization from a dimethylformamide/water mixture.

Workup

  1. filtrationThe product is then filtered off at 10° C.
  2. washwashed first with toluene
  3. dry with materialwith water, and dried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-cf1e41711acd46c5ae3c25f04409c1d6
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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