Ethyl isothiocyanatoformate → Ethyl N-[(2,3,5-tribromo-4-methoxy-phenyl)carbamothioyl]carbamate

HRID 712188Notes

Reaction equation

[Br:1][C:2]1[C:8]([Br:9])=[C:7]([O:10][CH3:11])[C:6]([Br:12])=[CH:5][C:3]=1[NH2:4].[CH2:13]([O:15][C:16]([N:18]=[C:19]=[S:20])=[O:17])[CH3:14]>CC(C)=O>[Br:1][C:2]1[C:8]([Br:9])=[C:7]([O:10][CH3:11])[C:6]([Br:12])=[CH:5][C:3]=1[NH:4][C:19]([NH:18][C:16](=[O:17])[O:15][CH2:13][CH3:14])=[S:20]

Participants

Conditions

Temperature: 40 °C

Procedure

2,3,5-Tribromo-4-methoxy-aniline (4.72 g, 13.1 mmol) was dissolved in acetone (150 mL) and ethoxycarbonyl isothiocyanate (1.63 mL, 14.4 mmol) was added. The solution was heated to 40° C. After 20 minutes a pale yellow precipitate had formed. The viscous mixture was cooled to rt and stirred at rt overnight. The solvent was removed under reduced pressure. Cyclohexane (˜150 mL) was added to the residue and the suspension sonicated. The solid was collected by filtration through a PTFE filter to give an off-white fluffy solid which was dried in the vacuum oven (40° C.) to afford the desired compound as an off-white solid, 6.00 g (93%). m/z: 488.78/490.80/492.75/494.80 [M+H]+.

Workup

customAfter 20 minutes a pale yellow precipitate had formed
temperatureThe viscous mixture was cooled to rt
customThe solvent was removed under reduced pressure
additionCyclohexane (˜150 mL) was added to the residue
customthe suspension sonicated
filtrationThe solid was collected by filtration through a PTFE
filtrationfilter
customto give an off-white fluffy solid which
customwas dried in the vacuum oven (40° C.)

Sources & evidence

ORD record: ord-b3d82cd6133946ccb3a23b2a34cff912
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181234B2

Reaction notes

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