Dimethyl-p-toluidine → 2-Chloro-4-(2,4-dimethoxy-benzyl)-7-bromo-3,4-dihydro-benzo[e][1,4]diazepin-5-one

HRID 351841Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:4]=1[CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([Br:18])[CH:16]=[CH:17][C:10]=2[NH:9][C:8](=O)[CH2:7]1.CN(C)C1C=CC(C)=CC=1.P(Cl)(Cl)([Cl:38])=O>C1(C)C=CC=CC=1>[Cl:38][C:8]1[CH2:7][N:6]([CH2:5][C:4]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:3]=2[O:2][CH3:1])[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([Br:18])[CH:16]=[CH:17][C:10]=2[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(2,4-Dimethoxy-benzyl)-7-bromo-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (3.0 g, 7.4 mmol) and N,N-dimethyl-p-toluidine (2.1 mL, 14.8 mmol) were mixed in toluene (30 mL) and heated to 100° C. Then phosphorus oxychloride (745 μL, 8.1 mmol) was added dropwise and heating at 100° C. was continued for 2.5 h. The resulting dark red solution was evaporated and the residue dissolved in THF (10 mL) and used directly in the subsequent step.

Workup

temperatureheating at 100° C.
customThe resulting dark red solution was evaporated
dissolutionthe residue dissolved in THF (10 mL)

Sources & evidence

ORD record: ord-6b8915960bd74c35be7caac5e7f40218
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743789B2

Reaction notes

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