Water → HCID 86705555, compound

HRID 2279569Notes

Reaction equation

HRID 2279569 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10][CH2:11]I)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:21][S-:22].[Na+].O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10][CH2:11][S:22][CH3:21])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 86705551HCID 86705551, compound

Product 1

HCID 86705555HCID 86705555, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 366 (810 mg, 1.88 mmol) and sodium methanethiolate (158 mg, 2.26 mmol) in DMSO (4 mL) was stirred at 50° C. overnight. The mixture was poured into water, extracted with EtOAc, washed with brine, dried (MgSO4), and concentrated in vacuo to afford 395 mg (60%) of (R)-tert-butyl 1-(3,4-dichlorophenyl)-3-(methylthio)propylcarbamate (372).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-743724e17c1a41bcb1e9a577307bb433
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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