Ammonia → 3-Benzyloxyphenyl isothiocyanate

HRID 2237606Notes

Reaction equation

HRID 2237606 reaction equation
N.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17](C1NC=CN=1)(C1NC=CN=1)=[S:18]>C(Cl)Cl.CCCCCC>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([N:13]=[C:17]=[S:18])[CH:14]=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 928923-BenzyloxyanilineHCID 11412697Thiocarbonyl diimidazole2×

Product 1

HCID 5614463-Benzyloxyphenyl isothiocyanateYield 84.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

The final product, Compound 1 is obtained by treatment of Z with thiocarbonyl di-imidazole followed by ammonia. 3-Benzyloxyaniline (5 g, 25 mmol) is added dropwise over a one minute period to 4.94 g (27.6 mmol) thiocabonyl di-imidazole in methylene chloride (150 ml). The resulting mixture is stirred at room temperature overnight. An additional 400 mg thiocarbonyl di-imidazole (TCDI) is added and the reaction is continued for 2 hours more. The reaction is diluted with hexane and filtered through silica. Concentration provides 5.1 g of the desired 3-benzyloxyphenyl isothiocyanate.

Workup

  1. waitthe reaction is continued for 2 hours
  2. filtrationfiltered through silica
  3. concentrationConcentration

Sources & evidence

ORD record
ord-8c055b9ef0ab49b6ae84f3f55f0fc9fa
Source dataset
uspto-grants-2010_05
Patent number
US07718671B2

Reaction notes

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