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

HRID 351837Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:4]=1[CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([CH:18]([CH3:20])[CH3:19])[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:40])=O>C1(C)C=CC=CC=1>[Cl:40][C:8]1[CH2:7][N:6]([CH2:5][C:4]2[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:3]=2[O:2][CH3:1])[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([CH:18]([CH3:20])[CH3:19])[CH:16]=[CH:17][C:10]=2[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(2,4-Dimethoxy-benzyl)-7-isopropyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (1.5 g, 4.1 mmol) and N,N-dimethyl-p-toluidine (1.76 mL, 12.2 mmol) were mixed in toluene (8 mL) and heated to 100° C. Then phosphorus oxychloride (559 μL, 6.1 mmol) was added dropwise and heating at 100° C. was continued for 2.5 h. After cooling, the mixture was evaporated and dissolved in THF (10 mL) and was used directly in the subsequent step.

Workup

temperatureheating at 100° C.
temperatureAfter cooling
customthe mixture was evaporated
dissolutiondissolved in THF (10 mL)

Sources & evidence

ORD record: ord-10a61c28142a4fa3ad5164a4f2173117
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743789B2

Reaction notes

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