Thionyl Chloride → HCID 19813434, compound

HRID 345036Notes

Reaction equation

HRID 345036 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[O:8][C:9]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]=2[C:11]=1[CH3:12]>C(Cl)Cl.N1C=CC=CC=1.O>[Cl:3][CH2:6][C:7]1[O:8][C:9]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]=2[C:11]=1[CH3:12]

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 19813433HCID 19813433, compound

Product 1

HCID 19813434HCID 19813434, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (1.48 g, 12.4 mmole) was added dropwise to a solution of 2-hydroxymethyl-3-methyl-5-nitrobenzofuran (0.86 g, 4.15 mmole) in methylene chloride (10 ml) and pyridine (2 drops) and the mixture was stirred at room temperature for 24 hours. The reaction mixture was then diluted with water, the organic phase separated, and the aqueous phase re-extracted with methylene chloride. The combined organic phases were washed with aqueous sodium bicarbonate, dried (Na2SO4) and the solvent evaporated to leave the title compound, 0.93 g. A portion was recrystallised from ethanol, m.p. 141°-142°.

Workup

  1. customthe organic phase separated
  2. extractionthe aqueous phase re-extracted with methylene chloride
  3. washThe combined organic phases were washed with aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-c64daf4c5ecd4af58522f7f0c9741671
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Reaction notes

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