Hydrochloric Acid → HCID 13787416, compound

HRID 414192Notes

Reaction equation

HRID 414192 reaction equation
C([Al](CC(C)C)CC(C)C)C(C)C.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21].[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O-:32])(=[O:31])=O)=[CH:25][CH:24]=1.[NH:33]1[C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([C:42](OC)=[O:43])[C:36]=2[CH:35]=[CH:34]1.Cl>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([O:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][C:42]([C:37]2[C:36]3[CH:35]=[CH:34][NH:33][C:41]=3[CH:40]=[CH:39][CH:38]=2)=[O:43])(=[O:31])=[O:32])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2733668methyl 1H-indole-4-carboxylateHCID 16682931TriisobutylaluminumHCID 86742610HCID 86742610, compound

Product 1

HCID 13787416HCID 13787416, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent2×

Procedure

140 ml of triisobutylaluminum in solution in toluene at 1.1 mole/l were added to a solution of 18 g of 2-aminophenol-4-methyl-benzenesulfonate in 300 ml of chloroform, and after stirring for 15 minutes, a solution of 12.15 g of methyl indol-4-carboxylate in 120 ml of chloroform was added. The mixture was refluxed for 20 hours and was then cooled to 0° to -10° C. and 500 ml of an N aqueous solution of hydrochloric acid were added with stirring over 15 minutes. The chloroform phase was then purified by chromatography over silica (eluent: methylene chloride) to obtain 25 g of N-[2-[(4-methylphenyl)sulfonyloxy]phenyl]-1H-indol-4-carboxamide melting at 135° C.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. temperaturewas then cooled to 0° to -10° C.
  3. stirringwith stirring over 15 minutes
  4. customThe chloroform phase was then purified by chromatography over silica (eluent: methylene chloride)

Sources & evidence

ORD record
ord-e45684d495434be798011a04fd15aae2
Source dataset
uspto-grants-1988_12
Patent number
US04791109

Reaction notes

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