Hydrochloric Acid → HCID 21705094, compound

HRID 1595459Notes

Reaction equation

HRID 1595459 reaction equation
C(=O)([O-])O.[Na+].C([O:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[C:13]([C:30]([O:32][CH3:33])=[O:31])[N:14]2[S:19]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=1)(=[O:21])=[O:20])(=O)C.Cl>CO>[Cl:29][C:24]1[CH:23]=[C:22]([S:19]([N:14]2[C:15]3[C:11](=[C:10]([OH:9])[CH:18]=[CH:17][CH:16]=3)[CH:12]=[C:13]2[C:30]([O:32][CH3:33])=[O:31])(=[O:21])=[O:20])[CH:27]=[CH:26][C:25]=1[Cl:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21705079HCID 21705079, compound

Product 1

HCID 21705094HCID 21705094, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous sodium hydrogencarbonate solution (16 ml, 50%) was added to methyl 4-acetoxy-N-(3,4-dichlorophenylsulphonyl)indole-2-carboxylate (0.63 g) in methanol (15 ml) and the reaction stirred for 48 hours at room temperature. The solution was then poured into 2M HCl and extracted with ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo to give the desired product as a gum (0.5 g, 87%); NMR δ (CD3SOCD3) 3.83 (s, 3H), 6.71 (d, 1H), 7.31 (t, 1H), 7.42-7.5 (m, 2H), 7.92 (s, 1H), 10.31 (s, 1H); M/z (+) 402 (MH+), 400.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialCombined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea27e9d252ea48f3a02fb5c71e88e8e9
Source dataset
uspto-grants-2001_09
Patent number
US06288103B1

Reaction notes

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