Water → Methyl 3-(benzothiazol-2-yl)-4,7-dimethylindole-2-carboxylate

HRID 361624Notes

Reaction equation

HRID 361624 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[CH:9][C:10]=2[CH3:12])[NH:5][C:4]=1[C:14]([O:16][CH3:17])=[O:15])=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25].O>C(OCC)(=O)C>[S:25]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:1]1[C:3]1[C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[CH:9][C:10]=2[CH3:12])[NH:5][C:4]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 87132-Aminothiophenol2×HCID 53886849Methyl 3-formyl-4,7-dimethylindole-2-carboxylate

Product 1

HCID 136124231Methyl 3-(benzothiazol-2-yl)-4,7-dimethylindole-2-carboxylateYield 20.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 10 ml of ethyl acetate were dissolved 0.50 g (2.16 mmol) of methyl 3-formyl-4,7-dimethylindole-2-carboxylate and 0.27 g (2.16 mmol) of o-aminothiophenol. The reaction mixture was stirred at room temperature overnight. After addition of 0.30 g of o-aminothiophenol, the reaction mixture was stirred for 1 day and then poured into water. The reaction mixture was extracted with diethyl ether, washed with water and concentrated. The crude crystals were purified by silica gel column chromatography (toluene) and recrystallized from methanol-water to provide 0.15 g of beige powder. Yield: 20%

Workup

  1. stirringthe reaction mixture was stirred for 1 day
  2. extractionThe reaction mixture was extracted with diethyl ether
  3. washwashed with water
  4. concentrationconcentrated
  5. customThe crude crystals were purified by silica gel column chromatography (toluene)
  6. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-c648be5bec5e493a849a33e6f95d0a67
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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