Methylamine → 1-(3,4-dichlorophenyl)-3-methylthiourea

HRID 1023186Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][C:3]=1[Cl:11].[CH3:12][NH2:13]>C(O)C>[Cl:11][C:3]1[CH:4]=[C:5]([NH:8][C:9]([NH:13][CH3:12])=[S:10])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 1,2-dichloro-4-isothiocyanatobenzene (1 g, 4.9 mmol) in ethanol (30 mL) was added 8M methyl amine in ethanol (0.613 mL, 4.9 mmol) and the reaction was heated at 80° C. overnight. The solvent was removed under vacuum and the residue was washed with diethyl ether (10 mL) and dried to give crude 1-(3,4-dichlorophenyl)-3-methylthiourea as an off white solid (0.8 g, 69%). 1HNMR: 400 MHz, DMSO-d6: δ 2.93 (d, J=4.40 Hz, 3H), 7.37 (d, J=7.60 Hz, 1H), 7.55 (d, J=8.40 Hz, 1H), 7.86 (d, J=2.40 Hz, 1H), 7.92 (bs, 1H), 9.74 (bs, 1H).

Workup

customThe solvent was removed under vacuum
washthe residue was washed with diethyl ether (10 mL)
customdried

Sources & evidence

ORD record: ord-ba1422761c6f4212891d4e08d313ca5d
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722670B2

Reaction notes

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