4-METHYL-1,3,4,5-TETRAHYDRO-2H-1,5-BENZODIAZEPIN-2-ONE → 74389-71-2

HRID 1485476Notes

Reaction equation

[CH3:1][CH:2]1[CH2:8][C:7](=O)[NH:6][C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[NH:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1COCC1>[CH3:1][CH:2]1[CH2:8][C:7](=[S:23])[NH:6][C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[NH:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A disposable tube was charged with 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (220 mg, 1.248 mmol) in THF (12 mL). Lawesson's Reagent (278 mg, 0.687 mmol) was added, and the solution was stirred at 80° C. 1 h. The solution was concentrated with celite and purified by silica gel chromatography to yield 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione as a yellow foam (0.163 g, 0.848 mmol, 68%).

Workup

custom1 h
concentrationThe solution was concentrated with celite
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-a0b5cace1dc4446f97a87074f57d342c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422292B2

Reaction notes

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