3-Chlorophenyl isothiocyanate → 1-(3-Chlorophenyl)-3-(2-phenyl-1-(pyridin-2-yl)-1-(3-(trifluoromethyl)phenyl)ethyl)thiourea

HRID 1365521Notes

Reaction equation

HRID 1365521 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)([NH2:15])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:26][C:27]1[CH:28]=[C:29]([N:33]=[C:34]=[S:35])[CH:30]=[CH:31][CH:32]=1>O1CCOCC1>[Cl:26][C:27]1[CH:28]=[C:29]([NH:33][C:34]([NH:15][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)[CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[S:35])[CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 754493-Chlorophenyl isothiocyanateHCID 66934553HCID 66934553, compound

Product 1

HCID 589202741-(3-Chlorophenyl)-3-(2-phenyl-1-(pyridin-2-yl)-1-(3-(trifluoromethyl)phenyl)ethyl)thiourea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1-(Pyridin-2-yl)-1-(3-(trifluoromethyl)phenyl)-2-phenylethanamine was dissolved in dioxane (40 uL, 0.5 M in dioxane, 20 umol) and 3-chlorophenylisothiocyanate was added (200 uL, 0.2 M in dioxane, 40 umol, 2.0 eq). The reaction mixture was agitated at room temperature for 18 h The solvent was evaporated and the residue was redissolved in 1 mL of MeOH and purified by reverse phase preparative HPLC using MeOH:water:TFA system. 1-(3-chlorophenyl)-3-(2-phenyl-1-(pyridin-2-yl)-1-(3-(trifluoromethyl)phenyl)ethyl)thiourea was obtained a colorless oil (13.9 umol, 69% yield). LCMS: M+calc=511.11; found=511.98.

Workup

  1. customwas evaporated
  2. dissolutionthe residue was redissolved in 1 mL of MeOH
  3. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-0af86d897ea84b25b2f207a3b951622e
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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