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

HRID 354762Notes

Reaction equation

HRID 354762 reaction equation
C(Br)CCC.FC1C=CC=CC=1C1C2C=C([N+]([O-])=O)C=CC=2N(C)C(=O)C(C)(C)N=1.C([N:35]1[C:41]2[C:42]([Cl:49])=[CH:43][C:44]([N+:46]([O-:48])=[O:47])=[CH:45][C:40]=2[C:39]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[F:56])=[N:38][C:37]([CH3:58])([CH3:57])[C:36]1=[O:59])CCC>>[Cl:49][C:42]1[C:41]2[NH:35][C:36](=[O:59])[C:37]([CH3:58])([CH3:57])[N:38]=[C:39]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=3[F:56])[C:40]=2[CH:45]=[C:44]([N+:46]([O-:48])=[O:47])[CH:43]=1

Participants

4

Reactant 3

HCID 8002Butyl bromideHCID 205061565-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-oneHCID 20506195HCID 20506195, compound

Product 1

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

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 n-butyl bromide there is obtained, in analogy to the details in paragraph (c) of Example 1, with a reaction period of 9 days and purification of the product by chromatography on silica gel (elution agent: methylene chloride), 1-butyl-9-chloro-5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 125°-127° (hexane/petroleum ether).

Sources & evidence

ORD record
ord-3d9df34fdb4849c28b42628372296e2c
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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