Cesium carbonate → HCID 19367647, compound

HRID 849675Notes

Reaction equation

HRID 849675 reaction equation
[CH3:1][C:2]1[C:10]2[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:9]=2[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([O:20]CC)=[O:19])[NH:6]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CO.O>[CH3:1][C:2]1[C:10]2[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:9]=2[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([OH:20])=[O:19])[NH:6]2

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 19367665HCID 19367665, compound

Product 1

HCID 19367647HCID 19367647, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 4-methyl-1H-[1]-benzothieno[2,3-f]indole-2-carboxylate (1.0 g, 3.2 mmol) was suspended in a mixture of methanol (110 ml) and water (30 ml). Caesium carbonate (10 g) was added and the mixture was heated at reflux under nitrogen for 2 h. The solution was allowed to cool to room temperature, and the methanol was removed in vacuo. The solution was acidified with 0.1 Molar Hydrochloric acid and the resulting yellow precipitate was collected by filtration and washed with water. The wet precipitate was dissolved in acetone and the solvent removed in vacuo to give the product as a yellow solid with m.p. 271-272° C.; δH [2H6 ]-DMSO 11.88 (1H, s, 1-NH), 8.29 (1H, dd, J 6, 3, 9-H), 8.18 (1H, s, 10-H), 7.89-7.99 (1H, m, 6-H), 7.44-7.54 (2H, m, 7-H, 8-H), 7.35 (1H, d, J 2, 3-H), 2.72 (3H, s, 4-CH3), m/z (%) 281 (90, M+), 263 (100) 235 (69).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under nitrogen for 2 h
  3. customthe methanol was removed in vacuo
  4. filtrationthe resulting yellow precipitate was collected by filtration
  5. washwashed with water
  6. dissolutionThe wet precipitate was dissolved in acetone
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c30056cb56774005a16bd3168b3fba85
Source dataset
uspto-grants-2000_01
Patent number
US06013807

Reaction notes

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