Triethylamine → 1-(2-isopropylphenyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)thiourea

HRID 62060Notes

Reaction equation

HRID 62060 reaction equation
Cl.[F:2][C:3]([F:25])([F:24])[O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[N:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][CH:17]=3)=[N:12]2)=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N:42]=[C:43]=[S:44])([CH3:35])[CH3:34]>ClCCl>[CH:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH:42][C:43]([NH:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[N:14]=[CH:15][N:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][C:3]([F:2])([F:24])[F:25])=[CH:10][CH:9]=3)[N:12]=2)=[CH:17][CH:18]=1)=[S:44])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1420522-Isopropylphenyl isothiocyanateHCID 118675148(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl) methanamine hydrochloride

Product 1

HCID 1186750431-(2-isopropylphenyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)thioureaYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 100 mL flask, to a solution of (4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl) methanamine hydrochloride (0.200 g, 0.598 mmol) in dichloromethane (5 mL) was added triethylamine (0.0720 g, 0.718 mmol) and 1-isopropyl-2-isothiocyanatobenzene (0.106 g, 0.598 mmol) in dichloromethane (5 mL) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated and the residue purified by flash column chromatography eluting with 10-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes as eluent to give the title compound as a white solid (0.145 g, 48%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by flash column chromatography
  3. washeluting with 10-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes as eluent

Sources & evidence

ORD record
ord-e991ed1b285e4aeea90a05925aa3c9b5
Source dataset
uspto-grants-2016_09
Patent number
US09445594B2

Reaction notes

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