1,2-Dichloro-4-isothiocyanatobenzene → HCID 86667922, compound

HRID 1752165Notes

Reaction equation

HRID 1752165 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].[Li]CCCC.[Cl:21][C:22]1[CH:23]=[C:24]([N:29]=[C:30]=[S:31])[CH:25]=[CH:26][C:27]=1[Cl:28]>C1COCC1>[Cl:21][C:22]1[CH:23]=[C:24]([NH:29][C:30]([N:7]([CH2:6][C:5]2[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:14])([F:15])[F:1])[CH:4]=2)[C:8]([NH2:10])=[O:9])=[S:31])[CH:25]=[CH:26][C:27]=1[Cl:28]

Participants

5

Reactant 3

HCID 230651,2-Dichloro-4-isothiocyanatobenzeneHCID 1487508HCID 1487508, compoundHCID 178418339Butyllithium

Product 1

HCID 86667922HCID 86667922, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-trifluoromethyl benzyl urea (218 mg, 1 mmol) in dry THF (2 mL) under nitrogen was added dropwise n-BuLi (2.5 M in hexane, 0.4 mL). The mixture was stirred at RT for 30 min and then 3,4-dichlorophenyl isothiocyanate (204 mg, 1 mmol) in dry THF (2 mL) was added dropwise. HPLC analysis after 5 min revealed complete reaction to the expected product. Saturated NaHCO3 (5 mL) and Et2O (15 mL) were added and the phases were separated. The aqueous phase was extracted with Et2O (2×15 mL). The combined organic phases were washed with brine (5 mL) and were dried over MgSO4. Concentration in vacuo gave 412 mg of a yellow oil. Purification by flash chromatography (silica, 20-30% EtOAc in n-hexane) gave 193 mg (46%) of pure product according to 1H NMR.

Workup

  1. waitHPLC analysis after 5 min revealed complete

Sources & evidence

ORD record
ord-28ef0e2bc8874b2681239291b933adad
Source dataset
uspto-grants-2015_10
Patent number
US09162994B2

Reaction notes

Loading…