Hydrochloric Acid → HCID 86745430, compound

HRID 1091126Notes

Reaction equation

HRID 1091126 reaction equation
C([Al](CC(C)C)CC(C)C)C(C)C.[NH2:14]C1C=CC=CC=1O.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O-:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.[NH:33]1[C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([C:42]([O:44]C)=O)[C:36]=2[CH:35]=[CH:34]1.Cl.[C:47]1(C)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C(Cl)(Cl)Cl>[CH3:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([O:32][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[C:34]2[NH:33][C:41]3[CH:40]=[CH:39][CH:38]=[C:37]([C:42]([NH2:14])=[O:44])[C:36]=3[CH:35]=2)(=[O:31])=[O:30])=[CH:27][CH:28]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 2733668methyl 1H-indole-4-carboxylateHCID 16682931TriisobutylaluminumHCID 86742610HCID 86742610, compound

Product 1

HCID 86745430HCID 86745430, compound

Reagents, catalysts & solvents 1

HCID 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-methylbenzenesulfonate 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-methylphenylsulfonyloxy]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-89fa226dedd446748279abe7535232ac
Source dataset
uspto-grants-1992_01
Patent number
US05084455

Reaction notes

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