5-Chloro-2-methylphenyl isothiocyanate → 3-(5-Chloro-2-methyl-phenyl)-1-ethyl-1-(1,3,5-trimethyl-1H-pyrazol-4-yl)-thiourea

HRID 2119805Notes

Reaction equation

HRID 2119805 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([N:8]=[C:9]=[S:10])[CH:7]=1.[CH2:12]([NH:14][C:15]1[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=1[CH3:20])[CH3:13]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([NH:8][C:9](=[S:10])[N:14]([CH2:12][CH3:13])[C:15]2[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=2[CH3:20])[CH:7]=1

Participants

3

Reactant 2

HCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 22335539N-Ethyl-1,3,5-trimethyl-1H-pyrazol-4-amine

Product 1

HCID 101318863-(5-Chloro-2-methyl-phenyl)-1-ethyl-1-(1,3,5-trimethyl-1H-pyrazol-4-yl)-thioureaYield 70%

Procedure

Prepared using Method A from 9.33 g (51 mmol) of 5-chloro-2-methyl-phenyl isothiocyanate and 4-ethylamino-1,3,5-trimethylpyrazole (7.2 g, 47 mmol) of step B to give 5.4 g of title compound as a white solid (70% yield, m.p. 144-145° C.). NMR (DMSO-d6, 400 MHz): 1.07 (t, 3H, CH2CH3), 2.04 (s, 3H, ArCH3), 2.07 (s, 3H, ArCH3), 2.11 (s, 3H, ArCH3), 3.82 (s, 3H, NCH3), 4.23 (m, 2H, CH2CH3), 7.02 (s, 1H, ArH), 7.19, (s, 2H, ArH), 8.41 (s, 1H, NH).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-20273f82b56b4fa1a9478447fe5dda39
Source dataset
uspto-grants-2004_02
Patent number
US06686476B2

Reaction notes

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