Water → HCID 11144375, compound

HRID 2293296Notes

Reaction equation

HRID 2293296 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([Cl:13])=[CH:9][C:10]=2[Cl:12])[NH:5][C:4]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:2].[H-].[Na+].[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C=O)C>[C:21]1([S:27]([N:5]2[C:6]3[C:11](=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=3)[C:3]([CH:1]=[O:2])=[C:4]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 2794948ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate

Product 1

HCID 11144375HCID 11144375, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of ethyl 3-formyl-4,6-dichloroindole-2-carboxylate (5.0 g) in dry DMF (30 ml) was added to a suspension of sodium hydride (0.629 g; 80% suspension in mineral oil) in dry DMF (10 ml) under nitrogen at 0°. The reaction was stirred at this temperature for 45 min then phenylsulfonyl chloride (2.5 ml) was added giving a yellow precipitate. The reaction was allowed to warm slowly to room temperature, stirred for a further 14 h then poured into water (250 ml). The solid was filtered, washed with water and then with ethyl acetate to give the title compound (4.493 g,) as a white solid, m.p. 225.8°-226.3°.

Workup

  1. customgiving a yellow precipitate
  2. stirringstirred for a further 14 h
  3. filtrationThe solid was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-ac7c1c60cd3046488673ec130afedb3e
Source dataset
uspto-grants-1997_11
Patent number
US05686461

Reaction notes

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