Benzoyl isothiocyanate → HCID 86667923, compound

HRID 1752167Notes

Reaction equation

HRID 1752167 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH2:6][NH:7][C:8]([NH2:10])=[O:9].[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH2:6][NH:7][C:8](=[O:9])[NH:10][C:25]([NH:24][C:16](=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[S:26]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 1487508HCID 1487508, compound

Product 1

HCID 86667923HCID 86667923, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(3-Trifluoromethyl-benzyl)-urea (218 mg; 1.0 mmol) and 163 mg (1.0 mmol) benzoylisothiocyanate were dissolved in acetone and the mixture was heated to reflux. After 18 h of reflux HPLC-MS revealed almost complete conversion to expected product in a very clean reaction. The solvent was evaporated and the residue was dissolved in EtOAc (40 mL). Wash with 2M HCl (5 mL), water (2×5 mL) and brine (5 mL), and the organic phase was dried over MgSO4 and concentrated in vacuo to give 347 mg of a light yellow solid. HPLC-MS indicates a purity of approximately 90%.

Workup

  1. temperaturethe mixture was heated to reflux

Sources & evidence

ORD record
ord-852fe42dfdb84fa987999e434905d59d
Source dataset
uspto-grants-2015_10
Patent number
US09162994B2

Reaction notes

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