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

HRID 354756Notes

Reaction equation

HRID 354756 reaction equation
C(N(CC)CCCl)C.FC1C=CC=CC=1C1C2C=C([N+]([O-])=O)C=CC=2N(C)C(=O)C(C)(C)N=1.[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]1[C:47]2[CH:48]=[C:49]([N+:52]([O-:54])=[O:53])[CH:50]=[CH:51][C:46]=2[N:45](CCN(CC)CC)[C:44](=[O:62])[C:43]([CH3:64])([CH3:63])[N:42]=1>CCOCC.CCCCCC>[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]1[C:47]2[CH:48]=[C:49]([N+:52]([O-:54])=[O:53])[CH:50]=[CH:51][C:46]=2[NH:45][C:44](=[O:62])[C:43]([CH3:64])([CH3:63])[N:42]=1

Participants

5

Reactant 3

HCID 13364Diethylaminoethyl chlorideHCID 205061485-(o-chlorophenyl)-1-(2-diethylaminoethyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-oneHCID 205061565-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-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-diethylaminoethyl chloride there is obtained, in analogy to the details in paragraph (c) of Example 1, with a reaction period of 60 hours, 5-(o-chlorophenyl)-1,3-dihyro-1-(2-diethylaminoethyl)-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 109° (ether/n-hexane).

Sources & evidence

ORD record
ord-6b67598530524fdabc37056985f36d87
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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