2-Pyrrolidone → 7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

HRID 354752Notes

Reaction equation

HRID 354752 reaction equation
N1CCCC1=O.[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:20]2[CH:21]=[C:22]([N:25]=C=O)[CH:23]=[CH:24][C:19]=2[N:18]([CH3:28])[C:17](=[O:29])[C:16]([CH3:31])([CH3:30])[N:15]=1.ClC1C=CC=CC=1C1C2C=C(NC(N3CCCC3)=O)C=CC=2N(C)C(=O)C(C)(C)N=1>C(OCC)(=O)C.CCOCC>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]2[N:18]([CH3:28])[C:17](=[O:29])[C:16]([CH3:31])([CH3:30])[N:15]=[C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[Cl:7])[C:20]=2[CH:21]=1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 20506146[5-(o-chlorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]isocyanateHCID 20506173N-[5-(o-chlorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-1-pyrrolidinecarboxamide

Product 1

HCID 205061787-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

From 5.1 g (0.015 mol) of 7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one and pyrrolidone there is obtained, in analogy to the details in Example 4, via [5-(o-chlorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]isocyanate, N-[5-(o-chlorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-1 -pyrrolidinecarboxamide of melting point 248°-150° (ethyl acetate/ether).

Sources & evidence

ORD record
ord-8b4d3083e2e744a19d4e567ea2a65631
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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