Thionyl Chloride → HCID 21428902, compound

HRID 437651Notes

Reaction equation

HRID 437651 reaction equation
O[CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6].S(Cl)([Cl:15])=O>>[ClH:15].[Cl:15][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2045999N-(2-Hydroxyethyl)picolinamide

Product 1

HCID 21428902HCID 21428902, compound

Procedure

To 49 parts of N-(2-hydroxyethyl)-2-pyridinecarboxamide are added dropwise 80 parts of sulfinyl chloride while stirring vigourously. Upon completion, stirring is continued first for 3 hours at reflux and further for 2 hours at room temperature. The excess of sulfinyl chloride is evaporated and the residue is poured onto hot methanol. After cooling, the precipitated product is filtered off (the filtrate is set aside) and washed thoroughly with 2,2'-oxybispropane, yielding a first fraction of 14 parts of N-(2-chloroethyl)-2-pyridinecarboxamide hydrochloride.

Workup

  1. stirringUpon completion, stirring
  2. customThe excess of sulfinyl chloride is evaporated
  3. additionthe residue is poured onto hot methanol
  4. temperatureAfter cooling
  5. filtrationthe precipitated product is filtered off (the filtrate
  6. washwashed thoroughly with 2,2'-oxybispropane

Sources & evidence

ORD record
ord-d29d4b933f24494d889baec150191e36
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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