Hydrochloric Acid → HCID 21699417, compound

HRID 2118537Notes

Reaction equation

HRID 2118537 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[S:11])=[CH:8][N:7]=1.[ClH:15]>>[CH3:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([Cl:15])=[S:11])=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 178425917HCID 178425917, compound

Product 1

HCID 21699417HCID 21699417, compound

Procedure

Thionylchloride (23.8 g) was added to 6-methylthionicotinic acid (15.3 g) (from the above referential example 1a). The reaction mixture was gradually heated with stirring and refluxed until the generation of hydrogen chloride ceased. 6-methylthionicotinoylchloride was stoichiometricly obtained by distilling off excess thionylchloride under reduced pressure. 6-methylthionicotinoylchloride dissolved in ether was added dropwise to 20% aqueous solution of sodium borohydride (6.5 g) at 0°~10° C. After adding, the mixture was stirred for one hour and the ether layer was separated and dried. The ether layer was evaporated under reduced pressure to give 2-methylthiopyridine-5-methanol (9.6 g). nD22 1.6084

Workup

  1. temperatureThe reaction mixture was gradually heated

Sources & evidence

ORD record
ord-ad3be0bbe5374163abc20fa303f4d8ee
Source dataset
uspto-grants-1987_07
Patent number
US04678795

Reaction notes

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