Thionyl Chloride → HCID 23354019, compound

HRID 235255Notes

Reaction equation

HRID 235255 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]1[N:13]([CH3:20])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:9]1=[N:8]2.S(Cl)([Cl:23])=O>C(Cl)Cl>[Cl:23][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]1[N:13]([CH3:20])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:9]1=[N:8]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23354014HCID 23354014, compound

Product 1

HCID 23354019HCID 23354019, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 304 mg (1.16 mmol) of 4-hydroxymethyl-6-methylindolo[2,3-b]quinoxaline in 30 ml of methylene chloride was added 0.126 ml (1.73 mmol, 1.5 eq.) of thionyl chloride under ice-cooling, followed by stirring for 3 hours. The reaction solution was poured into 50 ml of ice water, and extracted with methylene chloride. The organic layer was washed 3 times with a saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. Evaporation of the solvent gave 335 mg of the crude product 4-chloromethyl-6-methylindolo[2,3-b]quinoxaline, which was used for the next reaction without further purification.

Workup

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed 3 times with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-225ddbb399f8441698a0d365c8be3d82
Source dataset
uspto-grants-1997_01
Patent number
US05597921

Reaction notes

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