N-Methyl-4-(trifluoromethyl)aniline → N'-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-N-methyl-N-[4-(trifluoromethyl)phenyl]thiourea

HRID 1892111Notes

Reaction equation

HRID 1892111 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[N:8]=[C:7]([N:17]=[C:18]=[S:19])[N:6]=1.[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1>C(Cl)Cl>[F:21][C:2]([F:1])([F:20])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([F:15])([F:16])[F:14])[N:8]=[C:7]([NH:17][C:18](=[S:19])[N:23]([CH3:22])[C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=2)[N:6]=1

Participants

4

Reactant 2

HCID 15099755N-Methyl-4-(trifluoromethyl)anilineHCID 576518094,6-Bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl isothiocyanate

Product 1

HCID 57651721N'-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-N-methyl-N-[4-(trifluoromethyl)phenyl]thioureaYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl isothiocyanate (6.87 mmol) in CH2Cl2 (10 mL) was added N-methyl-4-trifluoromethylaniline (6.87 mmol) and the resulting solution was stirred at room temperature. After 18 h the solvent was evaporated and the crude material purified by chromatography (silica, hexane/EtOAc) to afford 131 as a yellow solid (2.15 g, 62% yield): m.p. 109-111° C.; 1H NMR (CDCl3) δ 7.76 (d, 2H, J=8.5), 7.46 (d, 3H, J=8.5 Hz), 5.96 (s, 1H), 4.77-4.68 (q, 4H, J=8.5 Hz); ESI/MS 509 (M+H), 507 (M−H).

Workup

  1. customAfter 18 h the solvent was evaporated
  2. customthe crude material purified by chromatography (silica, hexane/EtOAc)

Sources & evidence

ORD record
ord-487a6ef7d4724e58b5fcfc64b79b15a7
Source dataset
uspto-grants-2013_08
Patent number
US08507671B2

Reaction notes

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