2-Amino-5-bromobenzene-1-thiol → HCID 9951901, compound

HRID 1604276Notes

Reaction equation

HRID 1604276 reaction equation
[CH3:1][CH:2]1[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6](=[O:13])[CH2:5][C:4](=O)[CH2:3]1.[Br:15][C:16]1[CH:17]=[CH:18][C:19]([NH2:23])=[C:20]([SH:22])[CH:21]=1>CS(C)=O>[Br:15][C:16]1[CH:21]=[C:20]2[C:19](=[CH:18][CH:17]=1)[NH:23][C:4]1[CH2:3][CH:2]([CH3:1])[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6](=[O:13])[C:5]=1[S:22]2

Participants

4

Reactant 2

HCID 12090452-Amino-5-bromobenzene-1-thiolHCID 11148304HCID 11148304, compound2×

Product 1

HCID 9951901HCID 9951901, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of ethyl 6-methyl-2,4-dioxocyclohexane-1-carboxylate, 7b (5.94 g, 30 mmole) and 5-bromo-2-aminobenzenethiol, 6 (X=Br, 5.8 g, 30 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 separetely recrystallized twice from MeOH and proves to be identical. An analytical sample of 4k, (R=Br), mp 201-203° C. occurs as light orange crystals; 2.24 g (56.7%).

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 separetely recrystallized twice from MeOH

Sources & evidence

ORD record
ord-3fc60a38acd441a990f854a6f74f52e8
Source dataset
uspto-grants-1999_11
Patent number
US05994349

Reaction notes

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