Benzyl chloroformate → 1,3-Bis(benzyloxycarbonyl)-2-methylisothiourea

HRID 906224Notes

Reaction equation

HRID 906224 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].S(O)(O)(=O)=O.[CH3:17][S:18][C:19](=[NH:21])[NH2:20]>ClCCl>[CH2:5]([O:4][C:2]([NH:21][C:19](=[N:20][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])[S:18][CH3:17])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothioureaYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 ml (14.4 mol) of benzyl chloroformate are added dropwise, under vigorous stirring, to a solution of 1 g (3.60 mmol) of S-methylisothiourea sulphate in 40 ml of a diphasic mixture of dichloromethane/saturated aqueous sodium bicarbonate solution (1:1). Stirring is maintained at ambient temperature for 25 hours. After which, the aqueous phase is extracted 3 times with dichloromethane. The combined organic phases are then washed with water, then dried over sodium sulphate and evaporated under reduced pressure. The residue obtained is purified by chromatography on a silica column (DCM) in order to produce 1.06 g (82%) of product in the form of a yellow oil.

Workup

  1. extractionAfter which, the aqueous phase is extracted 3 times with dichloromethane
  2. washThe combined organic phases are then washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue obtained
  6. customis purified by chromatography on a silica column (DCM) in order

Sources & evidence

ORD record
ord-ae9c86c6036347b1880432f818c6c35f
Source dataset
uspto-grants-2011_09
Patent number
US08012985B2

Reaction notes

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