Hydrochloric Acid → HCID 67557336, compound

HRID 581058Notes

Reaction equation

HRID 581058 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]2[C:5]=1[C:6](/[CH:19]=[CH:20]/[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:8]2.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl>CN(C)C=O>[Cl:3][C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]2[C:5]=1[C:6](/[CH:19]=[CH:20]/[C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:8]2[S:34]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 10738773HCID 10738773, compound

Product 1

HCID 67557336HCID 67557336, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0:35 g) was dissolved in dry dimethylformamide (60 ml) and cooled at 0° then a solution of 4,6-dichloro-2ethoxycarbonyl-3-(E)-(2'-tert-butoxycarbonylethenyl)-1-H-indole (5.14 g) in dimethylformamide (40 ml) was added The reaction mixture was stirred for 45 min at 0° then phenylsulfonyl chloride (1.87 ml) was added and the solution stirred overnight at r.t. The solution was poured into a 0.5N aqueous solution of hydrochloric acid and extracted with ethyl acetate (400 ml). The organic phase was washed with a solution of sodium hydrogencarbonate and brine, then dried and evaporated obtaining the title compound as a yellow solid (6.64 g) Rf =0.78 (ethylacetate/cyclohexane=1/2 as eluant).

Workup

  1. temperaturecooled at 0°
  2. stirringthe solution stirred overnight at r.t
  3. extractionextracted with ethyl acetate (400 ml)
  4. washThe organic phase was washed with a solution of sodium hydrogencarbonate and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-ffec56d591b446fba193ff76473c30f4
Source dataset
uspto-grants-1999_07
Patent number
US05919811

Reaction notes

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