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

HRID 351828Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:10]=2[NH:9][C:8](=O)[CH2:7]1.CN(C)C1C=CC(C)=CC=1.[Cl-:37].[P+]=O>C1(C)C=CC=CC=1>[Cl:37][C:8]1[CH2:7][N:6]([CH2:5][C:4]2[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:3]=2[O:2][CH3:1])[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:10]=2[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(2,4-Dimethoxy-benzyl)-7-methoxy-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (23.7 g, 67 mmol) and N,N-dimethyl-p-toluidine (19.2 mL, 133 mmol) were mixed in toluene (200 mL) and heated to 100° C. Then phosphorous oxide chloride (6.7 mL, 73 mmol) was added dropwise and heating at 100° C. was continued for 2.5 h. The resulting dark red solution was evaporated to dryness and the residue redissolved in THF (150 mL) and used directly in the subsequent step.

Workup

temperatureheating at 100° C.
customThe resulting dark red solution was evaporated to dryness
dissolutionthe residue redissolved in THF (150 mL)

Sources & evidence

ORD record: ord-34ddf633144945fcbefccf782d031b7d
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743789B2

Reaction notes

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