Thionyl Chloride → HCID 67251397, compound

HRID 41601Notes

Reaction equation

HRID 41601 reaction equation
[CH3:1][C:2]1[N:3]([S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:4]2[C:9]([C:10]=1[CH2:11]O)=[CH:8][CH:7]=[CH:6][CH:5]=2.S(Cl)([Cl:25])=O>C(Cl)(Cl)Cl>[Cl:25][CH2:11][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([S:13]([C:16]2[CH:17]=[CH:18][C:19]([CH3:20])=[CH:21][CH:22]=2)(=[O:14])=[O:15])[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67250021HCID 67250021, compound

Product 1

HCID 67251397HCID 67251397, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of (2-methyl-1-tosyl-1H-indol-3-yl)methanol (500 mg, 1.59 mmol) in chloroform (20 mL), thionyl chloride (0.23 mL, 3.18 mmol) was added dropwise at 0° C. and stirred for 10 min. Then the mixture was heated under reflux for 3.5 h. The reaction mixture was concentrated under reduced pressure. The residue was taken up in diethyl ether and evaporated to dryness under reduced pressure to yield the title compound (550 mg, quant.). The compound was directly used for the next step without further purification. [TLC Rf=0.58 (ethyl acetate/hexane 20:80)].

Workup

  1. temperatureThen the mixture was heated
  2. temperatureunder reflux for 3.5 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7636fdfdb498462bb6c08eef1007c2e7
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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