Methanol → Methyl 5-chloro-3-phenylthioindole-2-carboxylate

HRID 260461Notes

Reaction equation

HRID 260461 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]([OH:19])=[S:18])=[C:11]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CO>C(Cl)(Cl)Cl>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]([O:19][CH3:1])=[S:18])=[C:11]2[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 178526153HCID 178526153, compound

Product 1

HCID 86749575Methyl 5-chloro-3-phenylthioindole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Oxalyl chloride (0.70 mL, 9.6 mmol) was added to a solution of 5-chloro-3-phenylthioindole-2-carboxylic acid (0.97 g, 3.2 mmol) in chloroform (50 mL) under nitrogen. The reaction was refluxed for 3 h, cooled and reduced to dryness in vacuo. The resulting solid was dissolved in chloroform and added to methanol at 0° C. The methanol was removed in vacuo and the crude product chromatographed on silica gel with 20% ethyl acetate in hexane. The title compound was obtained as a solid, mp 193°-196° C. Anal. Calc. for C16H12ClNO2S: C, 60.47; H, 3.81; N, 4.42. Found: C, 60.09; H, 3.50; N, 4.67.

Workup

  1. temperatureThe reaction was refluxed for 3 h
  2. temperaturecooled
  3. customThe methanol was removed in vacuo
  4. customthe crude product chromatographed on silica gel with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4b350406c5f24970a4b18f35fdeec2a5
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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