Benzoyl isothiocyanate → HCID 86641097, compound

HRID 1809599Notes

Reaction equation

HRID 1809599 reaction equation
[O:1]([C:8]1[C:9]([NH2:18])=[N:10][CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[C:19]([NH:27][C:28]([NH:18][C:9]1[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][C:12]([C:14]([F:17])([F:15])[F:16])=[CH:11][N:10]=1)=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 67487692HCID 67487692, compound

Product 1

HCID 86641097HCID 86641097, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

3-Phenoxy-5-(trifluoromethyl)pyridin-2-amine (0.472 g, 1.86 mmol) was combined with benzoyl isothiocyanate (0.376 mL, 2.79 mmol) and THF (5 mL). The mixture was heated to 55° C. and agitated overnight. The solvent was evaporated and the residue purified by column chromatography on silica gel, eluted with 10% ethyl acetate/hexane to afford 1-benzoyl-3-(3-phenoxy-5-(trifluoromethyl)pyridin-2-yl)thiourea (0.460 g, 59.4% yield) as white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography on silica gel
  3. washeluted with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c60dd9a9429c40fda86ebb5bca8289d7
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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