Ethyl Bromide → 9-chloro-5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

HRID 354765Notes

Reaction equation

HRID 354765 reaction equation
C(Br)C.FC1C=CC=CC=1C1C2C=C([N+]([O-])=O)C=CC=2N(C)C(=O)C(C)(C)N=1.[Cl:29][C:30]1[C:40]2[N:39](CC)[C:38](=[O:43])[C:37]([CH3:45])([CH3:44])[N:36]=[C:35]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[F:52])[C:34]=2[CH:33]=[C:32]([N+:53]([O-:55])=[O:54])[CH:31]=1>CCOCC.CCCCCC>[Cl:29][C:30]1[C:40]2[NH:39][C:38](=[O:43])[C:37]([CH3:45])([CH3:44])[N:36]=[C:35]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[F:52])[C:34]=2[CH:33]=[C:32]([N+:53]([O-:55])=[O:54])[CH:31]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 205061565-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-oneHCID 20506192HCID 20506192, compound

Product 1

HCID 205061649-chloro-5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

From 10 g (0.028 mol) of 9-chloro-5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one and ethyl bromide there is obtained, in analogy to the details in paragraph (c) of Example 1, with a reaction period of 8 days and chromatography of the crude product on silica gel (elution agent: methylene chloride), 9-chloro-1-ethyl-5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 117°-120° (ether/n-hexane).

Sources & evidence

ORD record
ord-ac9f6fcd0e8946d996068c08b667ab01
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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