Benzoyl chloride → HCID 59334954, compound

HRID 1517937Notes

Reaction equation

HRID 1517937 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+].[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(OCC)(=O)C>ClCCl>[C:32]([N:18]1[C:19]2[C:15](=[CH:14][C:13]([N:12]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[S:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)(=[O:11])=[O:10])=[CH:21][CH:20]=2)[CH:16]=[CH:17]1)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2×HCID 59276833HCID 59276833, compound

Product 1

HCID 59334954HCID 59334954, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mg tert.butyl [(3,5-dichloro-phenylsulphonyl)-(1H-indol-5-yl)-amino]-acetate are dissolved in 2 ml dichloromethane. 5 mg powdered sodium hydroxide and 19 μl benzoyl chloride are added. Then the mixture is stirred for 4 hours at ambient temperature, divided between 1 N sodium hydroxide solution and ethyl acetate, the aqueous phase is extracted with ethyl acetate and the combined organic phases are dried with magnesium sulphate. The solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 10:1 to 1:2).

Workup

  1. additionare added
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. dry with materialthe combined organic phases are dried with magnesium sulphate
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 10:1 to 1:2)

Sources & evidence

ORD record
ord-ebc86fdef5be44379624333628f45ce4
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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