2-Amino-5-chlorobenzenethiol → HCID 69821036, compound

HRID 1604271Notes

Reaction equation

HRID 1604271 reaction equation
[CH3:1][CH:2]1[CH:7]([C:8]([O:10][CH3:11])=[O:9])[C:6](=[O:12])[CH2:5][C:4](=O)[CH2:3]1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([NH2:22])=[C:19]([SH:21])[CH:20]=1>CS(C)=O>[Cl:14][C:15]1[CH:20]=[C:19]2[C:18](=[CH:17][CH:16]=1)[NH:22][C:4]1[CH2:3][CH:2]([CH3:1])[CH:7]([C:8]([O:10][CH3:11])=[O:9])[C:6](=[O:12])[C:5]=1[S:21]2

Participants

4

Reactant 2

HCID 27375182-Amino-5-chlorobenzenethiolHCID 4661376methyl 2-methyl-4,6-dioxocyclohexanecarboxylate2×

Product 1

HCID 69821036HCID 69821036, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of methyl 6-methyl-2,4-dioxocyclohexane-1-carboxylate, 7a (2.53 g, 13.7 mmole) and 5-chloro-2-aminobenzenethiol, 6 (X=Cl, 2.20 g, 13.7 mmole), in DMSO (10 mL) is placed in a preheated heating mantle. The reaction mixture is stirred and refluxed for 0.5 h. Upon cooling, the reaction mixture forms a solid. The crystals are filtered and the remaining mother liquid is poured into cold water, whereupon further precipitation occurs. Each precipitate is separately recrystallized twice from MeOH and proves to be identical. An analytical sample of 4e, (R=Cl), mp 226-227° C. occurs as light orange crystals; yield: 1.70 g (36.7%).

Workup

  1. temperaturerefluxed for 0.5 h
  2. temperatureUpon cooling
  3. filtrationThe crystals are filtered
  4. additionthe remaining mother liquid is poured into cold water, whereupon further precipitation
  5. customEach precipitate is separately recrystallized twice from MeOH

Sources & evidence

ORD record
ord-050601b6f903407ab2c2c8e833bfc8e3
Source dataset
uspto-grants-1999_11
Patent number
US05994349

Reaction notes

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