Ethyl orthoformate → Ro 14-7437

HRID 67514Notes

Reaction equation

HRID 67514 reaction equation
[NH2:1][C:2](=[C:8]1[CH2:14][N:13]([CH3:15])[C:12](=[O:16])[C:11]2[CH:17]=[CH:18][CH:19]=[CH:20][C:10]=2[NH:9]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:21](OCC)(OCC)OCC>C1(C)C=CC=CC=1>[CH3:15][N:13]1[C:12](=[O:16])[C:11]2[CH:17]=[CH:18][CH:19]=[CH:20][C:10]=2[N:9]2[CH:21]=[N:1][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]2[CH2:14]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 70541641ethyl alpha-amino-1,3,4,5-tetrahydro-4-methyl-5-oxo-2H-1,4-benzodiazepin-2-ylidene-acetate

Product 1

HCID 127597Ro 14-7437

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.10 g of ethyl α-amino-1,3,4,5-tetrahydro-4-methyl-5-oxo-2H-1,4-benzodiazepin-2-ylidene-acetate are dissolved in 15 ml of toluene and treated with 1.0 ml of triethyl orthoformate. The mixture is heated to reflux for 50 minutes, subsequently cooled and evaporated in vacuo. The crystalline residue is suspended in 25 ml of ethyl acetate, filtered off and dried. There is obtained ethyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 165° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 50 minutes
  3. temperaturesubsequently cooled
  4. customevaporated in vacuo
  5. filtrationfiltered off
  6. customdried

Sources & evidence

ORD record
ord-95ae50f00a004a46b0fabb7c166681a4
Source dataset
uspto-grants-1982_08
Patent number
US04346033

Reaction notes

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