Ethyl Acetate → Ro 14-7437

HRID 67416Notes

Reaction equation

HRID 67416 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-32c057f33fe8443b8fa26c09929fe402
Source dataset
uspto-grants-1982_08
Patent number
US04346032

Reaction notes

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