Sulfuryl chloride → 2-Chloro-3-phenylthioindole

HRID 1906938Notes

Reaction equation

HRID 1906938 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6]1([S:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[Cl:4][C:14]1[NH:15][C:16]2[C:21]([C:13]=1[S:12][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 8524893-Phenylthioindole

Product 1

HCID 134429412-Chloro-3-phenylthioindole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfuryl chloride (0.07 ml, 0.119 g, 0.88 mmol) was added dropwise at 0° to a stirred solution of 3-phenylthioindole (0.200 g, 0.88 mmol) in dry dichloromethane (20 ml). After 1 h the reaction mixture was washed with saturated sodium bicarbonate solution, the organic phase was dried and evaporated in vacuo. The residue was subjected to thin layer chromatography on silica gel eluting the product with hexane-ethyl acetate (7:3). There was obtained the desired product which had m.p. 98°-99° after crystallization from dichloromethane-pentane, and was identical to the material prepared in Example 13.

Workup

  1. washAfter 1 h the reaction mixture was washed with saturated sodium bicarbonate solution
  2. customthe organic phase was dried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-aec3f2c422fe4b6c9509643c55bd68c0
Source dataset
uspto-grants-1987_03
Patent number
US04654360

Reaction notes

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