Thionyl Chloride → HCID 13662994, compound

HRID 648031Notes

Reaction equation

HRID 648031 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]([C:9]1[S:13][C:12]2[CH:14]=[C:15]([CH2:18]O)[CH:16]=[CH:17][C:11]=2[C:10]=1[CH3:20])=[O:8]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:5][O:6][C:7]([C:9]1[S:13][C:12]2[CH:14]=[C:15]([CH2:18][Cl:3])[CH:16]=[CH:17][C:11]=2[C:10]=1[CH3:20])=[O:8]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 13662989HCID 13662989, compound

Product 1

HCID 13662994HCID 13662994, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6212ChloroformSolvent

Procedure

Thionyl chloride (0.75 ml.) was added cautiously to a solution of 6-hydroxymethyl-3-methylbenzo[b]-thiophene-2-carboxylic acid methyl ester (0.70 g.) and pyridine (3 drops) in chloroform (7.5 ml.) and the resulting solution was allowed to stand for 1 hour. It was then washed successively with water, sodium bicarbonate solution and dried (Na2SO4). Evaporation of the solvent gave a solid which was crystallized from petrol (b.p. 60°-80°) to give 6-chloromethyl-3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester (0.63 g.), m.p. 128°-129° C.

Workup

  1. washIt was then washed successively with water, sodium bicarbonate solution
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of the solvent
  4. customgave a solid which
  5. customwas crystallized from petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-22870eba54b14f1bbe67393f26b8513e
Source dataset
uspto-grants-1983_10
Patent number
US04410539

Reaction notes

Loading…