Thiophosgene → 4-Benzyloxyphenyl isothiocyanate

HRID 1464061Notes

Reaction equation

HRID 1464061 reaction equation
[C:1](Cl)(Cl)=[S:2].C(=O)([O-])[O-].[Ca+2].[CH2:10]([O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl.O>[CH2:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]([N:22]=[C:1]=[S:2])=[CH:23][CH:24]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 228604-Benzyloxyaniline

Product 1

HCID 27355034-Benzyloxyphenyl isothiocyanate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
15 °C

Procedure

Thiophosgene (12.63 g) was added at 0° C. to a stirred suspension of calcium carbonate (11.05 g) in a mixture of dichloromethane (100 ml) and water (100 ml). A solution of p-benzyloxyaniline (16.5 g) in dichloromethane (100 ml) was added dropwise at 0° C. over 30 minutes. The mixture was stirred for four hours at 15° C. The organic layer was separated, dried and the solvent removed by evaporation to give a residue which was extracted into boiling hexane to give 4-benzyloxyphenylisothiocyanate (m.p. 69° C.).

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customthe solvent removed by evaporation
  4. customto give a residue which
  5. extractionwas extracted

Sources & evidence

ORD record
ord-f15e01491a9943a58e14f7a09a363dc3
Source dataset
uspto-grants-1994_04
Patent number
US05302720

Reaction notes

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