Water → HCID 23458559, compound

HRID 1679931Notes

Reaction equation

HRID 1679931 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.CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1.O>C(O)(=O)C>[N:1]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)[CH:18]=[CH:22][CH:21]=[CH:20]1

Participants

5

Reactant 3

HCID 962WaterHCID 790982,5-DimethoxytetrahydrofuranHCID 202648445-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one

Product 1

HCID 23458559HCID 23458559, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.0 g (49.7 millimoles) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one (see Example 8a), 6.6 g (49.9 millimoles) of 2,5-dimethoxytetrahydrofuran and 100 ml of acetic acid are refluxed for 4 hours. The product is filtered off at 10° C. and recrystallized from a dimethylformamide/water mixture. 5.2 g (41% of theory) of 2-[p-(pyrrol-1-yl)-phenyl]-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 beige crystals, of melting point 230°-231° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. customrecrystallized from a dimethylformamide/water mixture

Sources & evidence

ORD record
ord-fbcc278de2fe4689a6d6453baca5a1f8
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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