Benzyl Isothiocyanate → HCID 59094529, compound

HRID 1168291Notes

Reaction equation

HRID 1168291 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]([NH:15][NH2:16])=[O:14])[O:4]1.[CH2:17]([N:24]=[C:25]=[S:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl>[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]([NH:15][NH:16][C:25](=[S:26])[NH:24][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:14])[O:4]1

Participants

4

Reactant 2

HCID 2346Benzyl IsothiocyanateHCID 59094493HCID 59094493, compound

Product 1

HCID 59094529HCID 59094529, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbohydrazide (Preparation 16) (4 g, 17.2 mmol) and benzyl isothiocyanate (2.38 ml, 18 mmol) in dichloromethane (50 ml) was stirred at room temperature for 12 hours. The solvent was removed by evaporation under reduced pressure and the residue was partioned between dichloromethane (100 ml) and water (100 ml). The organic layer was separated, dried (anhydrous magnesium sulphate) and evaporated under reduced pressure to give the title compound (5.90 g) which was used without further purification.

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customThe organic layer was separated
  3. dry with materialdried (anhydrous magnesium sulphate)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b2f67f078f9846eb842abcbda647c358
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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