Ethyl Acetate → Ro 14-7437

HRID 67614Notes

Reaction equation

HRID 67614 reaction equation
[NH2:1][C:2](=[C:8]1CNC(=O)[C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=2[NH:9]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(O[CH:23]([O:27]CC)[N:24]([CH3:26])[CH3:25])C.[C:30](OCC)(=O)C>>[CH3:26][N:24]1[C:23](=[O:27])[C:19]2[CH:18]=[CH:17][CH:16]=[CH:11][C:10]=2[N:9]2[CH:30]=[N:1][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]2[CH2:25]1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 70913Dimethylformamide diethylacetalHCID 70542724ethyl alpha-amino-1,3,4,5-tetrahydro-5-oxo-2H-1,4-benzodiazepin-2-ylidene-acetate

Product 1

HCID 127597Ro 14-7437

Procedure

4.1 g of ethyl α-amino-1,3,4,5-tetrahydro-5-oxo-2H-1,4-benzodiazepin-2-ylidene-acetate are dissolved in 25 ml of ethyl acetate, treated with 3.1 ml (18.1 mmol) of N,N-dimethylformamide diethyl acetal and heated to boiling under reflux for 0.5 hour. After cooling, the separated material is filtered off under suction and recrystallised form ethanol. After chromatography of the mother liquor, there is obtained a second portion of ethyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of the same purity; melting point 166°-168° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 0.5 hour
  3. temperatureAfter cooling
  4. filtrationthe separated material is filtered off under suction
  5. customrecrystallised
  6. customform ethanol

Sources & evidence

ORD record
ord-c8479e067ac844ac8b12d4a93276af7f
Source dataset
uspto-grants-1982_08
Patent number
US04346036

Reaction notes

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