N,N-Dimethylaniline → 5-Chloro-7,8-dimethoxy-1-methyl-1,3-dihydro-1,4-benzodiazepin-2-one

HRID 1297096Notes

Reaction equation

HRID 1297096 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[N:12]([CH3:13])[C:11](=[O:14])[CH2:10][NH:9][C:8](=O)[C:7]=2[CH:16]=1.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:30].C(Cl)Cl>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:30][C:8]1[C:7]2[CH:16]=[C:3]([O:2][CH3:1])[C:4]([O:17][CH3:18])=[CH:5][C:6]=2[N:12]([CH3:13])[C:11](=[O:14])[CH2:10][N:9]=1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 691555977,8-dimethoxy-1-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione

Product 1

HCID 691548525-Chloro-7,8-dimethoxy-1-methyl-1,3-dihydro-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Heat at 125° C. in a sealed tube for 3Y4 hour a solution of 100 mg (0.40 mmol) of 7,8-dimethoxy-1-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (XVIIaa), 280 μl of dimethylaniline, 800 μl of POCl3, in 10 ml of anhydrous CHCl3. Allow to cool to room temperature. Add 3 g of silica and 5 ml of CH2Cl2. Add at 0° C., 1 ml of triethylamine.

Workup

  1. additionAdd at 0° C.

Sources & evidence

ORD record
ord-70924f78099548cd8820a2a050bcdd2a
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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