2-Cyanoacetyl chloride → 2-[p-(Cyanoacetylamino)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one hemihydrate

HRID 463658Notes

Reaction equation

HRID 463658 reaction equation
[C:1]([CH2:3][C:4](Cl)=[O:5])#[N:2].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]3[CH:17]([C:18](=[O:21])[NH:19][N:20]=2)[CH2:16]3)=[CH:10][CH:9]=1>O1CCCC1>[OH2:5].[C:1]([CH2:3][C:4]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]3[CH:17]([C:18](=[O:21])[NH:19][N:20]=2)[CH2:16]3)=[CH:12][CH:13]=1)=[O:5])#[N:2].[C:1]([CH2:3][C:4]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]3[CH:17]([C:18](=[O:21])[NH:19][N:20]=2)[CH2:16]3)=[CH:12][CH:13]=1)=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 110515942-Cyanoacetyl chlorideHCID 202648445-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one

Product 1

HCID 704886982-[p-(Cyanoacetylamino)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one hemihydrateYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.6 g (54.1 millimoles) of cyanoacetyl chloride were added dropwise to 6.0 g (29.8 millimoles) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one in 150 ml of absolute tetrahydrofuran at room temperature, while stirring. After the addition was complete, stirring was continued for a further 10 minutes at 50° C. The product was filtered off under suction at 10° C., washed first with tetrahydrofuran and then with water and recrystallized from dimethylformamide/water. 3.6 g (44%) of 2-[p-(cyanoacetylamino)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one hemihydrate were obtained as pale beige crystals. Mp.: 284° C. (decomposition).

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. filtrationThe product was filtered off under suction at 10° C.
  4. washwashed first with tetrahydrofuran
  5. customwith water and recrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-fa6b089bc1c044fd9effb2cf600df465
Source dataset
uspto-grants-1985_10
Patent number
US04544562

Reaction notes

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