Sulfuryl chloride → HCID 22627321, compound

HRID 278097Notes

Reaction equation

HRID 278097 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1)[CH3:2].S(Cl)([Cl:19])(=O)=O>ClCCl>[Cl:19][C:4]1[NH:5][C:6]2[C:11]([C:3]=1[CH2:1][CH3:2])=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=2

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 22627226HCID 22627226, compound

Product 1

HCID 22627321HCID 22627321, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of methyl 3-ethylindole-6-carboxylate (138 mg) in dichloromethane (5 ml) was added sulfuryl chloride (0.066 ml), and the mixture was stirred at 20° C. for 1 hour. The resulting mixture was poured into ice and extracted with ethyl acetate. The combined organic phase was washed with aqueous sodium bicarbonate and brine, then dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (4:1) to give methyl 2-chloro-3-ethylindole-6-carboxylate (58.2 mg) as a solid.

Workup

  1. additionThe resulting mixture was poured into ice
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-4dc12eeac7f94100b3595ece94fb4620
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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