Sulfuryl chloride → 7-Chloromethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester

HRID 412531Notes

Reaction equation

HRID 412531 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22]SC)=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:28])(=O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][Cl:28])=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 60064133HCID 60064133, compound

Product 1

HCID 299251057-Chloromethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-methylthiomethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester (200 mg) in methylene chloride (4 ml) was dropwise added sulfuryl chloride (0.052 ml) with ice-cooling and under an argon atmosphere, and the mixture was stirred at the same temperature for 1 hour. The solvent was evaporated azeotropically with toluene and the residue was dried under reduced pressure to give the title compound (213 mg).

Workup

  1. temperaturecooling and under an argon atmosphere
  2. customThe solvent was evaporated azeotropically with toluene
  3. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-415ffef6915842ab9fee1c0f48febd25
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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