Pyridine → HCID 23303938, compound

HRID 1741261Notes

Reaction equation

HRID 1741261 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9]Cl.Cl[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([NH2:22])[C:17]=1[C:18]([O:20][CH3:21])=[O:19].N1C=CC=CC=1>ClCCl>[Cl:9][C:15]1[CH:14]=[CH:13][CH:12]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[C:16]=1[N:22]=[S:7]([CH3:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7520ThioanisoleHCID 24526ChlorineHCID 592849Methyl 2-amino-6-chlorobenzoate2×

Product 1

HCID 23303938HCID 23303938, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.0 g (24 mmol) of methyl phenyl sulfide in 30 mL of dichloromethane was cooled to -10° C. and 1.7 g (24 mmol) of chlorine was sparged in with cooling and stirring. To this was added with cooling and stirring 4.5 g (24 mmol) of solid methyl 6-chloroanthranilate and then 3.8 g (48 mmol) of pyridine. The product mixture contained the title compound and methyl 6-chloroanthranilate in a 60:40 ratio as determined by HPLC.

Workup

  1. temperaturewith cooling
  2. additionTo this was added
  3. temperaturewith cooling

Sources & evidence

ORD record
ord-1b5ce8b8d5474ecb894b2fd39c6ab199
Source dataset
uspto-grants-1999_10
Patent number
US05973148

Reaction notes

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