3-(Methylthio)phenyl isocyanate → HCID 19967389, compound

HRID 976633Notes

Reaction equation

HRID 976633 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH2:12]([O:19][NH:20][CH3:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1>[CH2:12]([O:19][N:20]([CH3:21])[C:10]([NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([S:2][CH3:1])[CH:4]=1)=[O:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 1414183-(Methylthio)phenyl isocyanateHCID 13417387(Benzyloxy)(methyl)amine

Product 1

HCID 19967389HCID 19967389, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(Methylthio)phenyl isocyanate (2.0 g, 12 mmol) was added dropwise to a solution of N-benzyloxy-N-methylamine (1.55 g, 11.3 mmol) in tetrahydrofuran (25 mL). The reaction mixture was stirred at ambient temperature for 2 hours then concentrated under vacuum. The residue was purified by flash chromatography (silica gel; ethyl acetate:hexanes) to provide 3.26 g of 1-benzyloxy-1-methyl-3-[3(methylthio)phenyl]urea as an oil.

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue was purified by flash chromatography (silica gel; ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-407e33eb86434d8da4c4123152557da1
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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