2-Bromoethanol → 5-(o-chlorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

HRID 354755Notes

Reaction equation

HRID 354755 reaction equation
BrCCO.FC1C=CC=CC=1C1C2C=C([N+]([O-])=O)C=CC=2N(C)C(=O)C(C)(C)N=1.[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[C:43]2[CH:44]=[C:45]([N+:48]([O-:50])=[O:49])[CH:46]=[CH:47][C:42]=2[N:41](CCO)[C:40](=[O:54])[C:39]([CH3:56])([CH3:55])[N:38]=1>CCOCC.CCCCCC>[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[C:43]2[CH:44]=[C:45]([N+:48]([O-:50])=[O:49])[CH:46]=[CH:47][C:42]=2[NH:41][C:40](=[O:54])[C:39]([CH3:56])([CH3:55])[N:38]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 205061565-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-oneHCID 205061795-(o-chlorophenyl)-1,3-dihydro-1-(2-hydroxyethyl)-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 205061685-(o-chlorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

From 25 g (0.073 mol) of 5-(o-chlorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one and 2-bromoethanol there is obtained, in analogy to the details in paragraph (c) of Example 1, with a reaction period of 7 days, 5-(o-chlorophenyl)-1,3-dihydro-1-(2-hydroxyethyl)-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 124°-125° (ether/n-hexane).

Sources & evidence

ORD record
ord-56b4f6ef3aad4d25a99ff8b4709fbf1e
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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