2-Amino-5-methylbenzene-1-thiol → HCID 9818412, compound

HRID 1604273Notes

Reaction equation

HRID 1604273 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.[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([NH2:23])=[C:20]([SH:22])[CH:21]=1>CS(C)=O>[C:8]([CH:7]1[C:6](=[O:13])[C:5]2[S:22][C:20]3[C:19](=[CH:18][CH:17]=[C:16]([CH3:15])[CH:21]=3)[NH:23][C:4]=2[CH2:3][CH:2]1[CH3:1])([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 3232602-Amino-5-methylbenzene-1-thiolHCID 11148304HCID 11148304, compound2×

Product 1

HCID 9818412HCID 9818412, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of ethyl 6-methyl-2,4-dioxocyclohexane-1-carboxylate, 7b (1.43 g, 7.2 mmole) and 5-methyl-2-aminobenzenethiol, 6 (X=Me, 1.0 g, 7.2 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 EtOH and proves to be identical. An analytical sample of 4i, (R=Me), mp 224° C. occurs as light orange crystals; yield: 0.50 (21.9%).

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 EtOH

Sources & evidence

ORD record
ord-5fbdaadb409c4891b807a2448de0c5c3
Source dataset
uspto-grants-1999_11
Patent number
US05994349

Reaction notes

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