Benzenesulfonyl chloride → HCID 10087048, compound

HRID 635374Notes

Reaction equation

HRID 635374 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CCC(=O)C.O>[C:14]1([S:20]([N:1]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=3[CH:3]=[CH:2]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chloride2×HCID 11430Potassium Carbonate2×HCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 10087048HCID 10087048, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of methyl indole-4-carboxylate (J. Org. Chem. 1980, 45, 3350) (5.0 g, 28.5 mmol), benzenesulphonyl chloride (10.1 g, 57.1 mmol) and anhydrous potassium carbonate (15.78 g, 114 mmol) in butan-3-one (150 ml) was refluxed under nitrogen for 15 hours. Additional benzenesulphonyl chloride (10.1 g) and anhydrous potassium carbonate (10.1 g) were added and refluxing was continued for 5 hours. The mixture was diluted with water (300 ml) and extracted with diethyl ether (3×300 ml). The combined organic solutions were dried (MgSO4) and concentrated to give a white solid which was recrystallised from ethanol (6.35 g, 72%); δH (360 MHz, CDCl3), 8.21 (1H, d, J=8.3 Hz, Ar—H), 7.96 (1H, dd, J=8.1 and 0.7 Hz, Ar—H), 7.87-7.84 (2H, m, Ar—H), 7.69 (1H, d, J=3.7 Hz, Ar—H), 7.56-7.33 (5H, m, Ar—H), 3.94 (3H, s, —OMe); m/z (CI) 316 (M++1).

Workup

  1. temperaturewas refluxed under nitrogen for 15 hours
  2. temperaturerefluxing
  3. extractionextracted with diethyl ether (3×300 ml)
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. concentrationconcentrated
  6. customto give a white solid which
  7. customwas recrystallised from ethanol (6.35 g, 72%)

Sources & evidence

ORD record
ord-0716f024237e42bb979c1abdc6a5630c
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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