Thionyl Chloride → HCID 19813434, compound

HRID 1031974Notes

Reaction equation

HRID 1031974 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-ca54a74d83be4f3898e0c2945b2388f9
Source dataset
uspto-grants-1990_09
Patent number
US04956382

Reaction notes

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