Thionyl Chloride → 1-Benzyl-2-chloro-3-phenylthioindole

HRID 1906937Notes

Reaction equation

HRID 1906937 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([S:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=O)=[CH:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([S:21][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:13]1[Cl:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 134429351-Benzyl-3-phenylsulfinylindole

Product 1

HCID 138001601-Benzyl-2-chloro-3-phenylthioindole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of thionyl chloride (0.03 ml, 0.054 g, 0.45 mmol) in dry dichloromethane (5 ml) was added dropwise to a stirred solution of 1-benzyl-3-phenylsulfinylindole (0.150 g, 0.45 mmol) in dry dichloromethane (20 ml), containing suspended sodium bicarbonate (1 g), maintained at 0° C. One half hour after the addition was completed the reaction was quenched with a saturated solution of aqueous sodium bicarbonate. The organic phase was separated, combined with a dichloromethane extract of the aqueous phase and the combined organic phases were dried and evaporated in vacuo. Crystallization of the residue from dichloromethane/hexane gave the title product.

Workup

  1. additioncontaining
  2. additionOne half hour after the addition
  3. customwas quenched with a saturated solution of aqueous sodium bicarbonate
  4. customThe organic phase was separated
  5. extractionextract of the aqueous phase
  6. customthe combined organic phases were dried
  7. customevaporated in vacuo
  8. customCrystallization of the residue from dichloromethane/hexane

Sources & evidence

ORD record
ord-45bee124a48c4548bd22dc9a71fcc562
Source dataset
uspto-grants-1987_03
Patent number
US04654360

Reaction notes

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