Hydrochloric Acid → HCID 59335041, compound

HRID 1517932Notes

Reaction equation

HRID 1517932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][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.CN(C1C=CC=CN=1)C.[CH2:31]([N:38]=[C:39]=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>ClCCl.C(OCC)(=O)C>[CH2:31]([NH:38][C:39]([N:18]1[C:19]2[C:15](=[CH:14][C:13]([NH:12][S:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)(=[O:11])=[O:10])=[CH:21][CH:20]=2)[CH:16]=[CH:17]1)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 76639Benzyl isocyanateHCID 25044530HCID 25044530, compound

Product 1

HCID 59335041HCID 59335041, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

130 mg 3,5-dichloro-N-(1H-indol-5-yl)-phenylsulphonamide are dissolved in 5 ml dichloromethane and 14 mg dimethylaminopyridine and 56 μl benzylisocyanate are added. The mixture is stirred overnight at ambient temperature, divided between 1 N HCl 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 1:3).

Workup

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

Sources & evidence

ORD record
ord-92d7d2ac1d934c99873e90e732a4ba46
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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