Thiophosgene → HCID 83290701, compound

HRID 911049Notes

Reaction equation

HRID 911049 reaction equation
[C:1](Cl)(Cl)=[S:2].[Cl:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([CH3:13])[N:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:5][C:6]1[C:11]([N:12]=[C:1]=[S:2])=[CH:10][CH:9]=[C:8]([CH3:13])[N:7]=1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 27344153-Amino-2-chloro-6-picoline

Product 1

HCID 83290701HCID 83290701, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of thiophosgene (3.871 g, 33.66 mmol) in dichloromethane (10 mL) was added to a mixture of 2-chloro-6-methylpyridin-3-amine (4.00 g, 28.05 mmol) and sodium carbonate (5.947 g, 56.11 mmol) in dichloromethane (200 mL). The reaction was stirred overnight at ambient temperature, then washed with water, brine, dried, and concentrated to afford the desired product (5.2 g, 100.4% yield) as a tan powder.

Workup

  1. washwashed with water, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e515da91033240fd815f2057ec29fb8d
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…