Methoxyacetyl chloride → 2-[p-(Methoxyacetylamino)-phenyl]-3,4-diazabicyclo[4.1.0]hept-2-en-5-one

HRID 463652Notes

Reaction equation

HRID 463652 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.[CH3:16][O:17][CH2:18][C:19](Cl)=[O:20]>O1CCCC1>[CH3:16][O:17][CH2:18][C:19]([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:20]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 202648445-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one

Product 1

HCID 131933752-[p-(Methoxyacetylamino)-phenyl]-3,4-diazabicyclo[4.1.0]hept-2-en-5-oneYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.0 g (29.8 millimoles) of 2-(p-aminophenyl)- 3,4-diazabicyclo[4.1.0]hept-2-en-5-one and 3.9 g (35.9 millimoles) of methoxyacetyl chloride in 150 ml of absolute tetrahydrofuran were refluxed for 4 hours, while stirring. The product was filtered off under suction at 10° C., washed first with tetrahydrofuran and then with water and recrystallized from propanol. 3.5 g (43%) of 2-[p-(methoxyacetylamino)-phenyl]-3,4-diazabicyclo[4.1.0]hept-2-en-5-one were obtained as colorless crystals. Mp.: 206° C.

Workup

  1. filtrationThe product was filtered off under suction at 10° C.
  2. washwashed first with tetrahydrofuran
  3. customwith water and recrystallized from propanol

Sources & evidence

ORD record
ord-ecb5692a2c3f4308b84c2ea5d73845c0
Source dataset
uspto-grants-1985_10
Patent number
US04544562

Reaction notes

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