Hydrochloric Acid → HCID 86735244, compound

HRID 614393Notes

Reaction equation

HRID 614393 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9]O)[C:5]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])=[CH:4][N:3]=1.[Na].C(=S)=[S:18].[ClH:20]>C(O)C>[ClH:20].[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][SH:18])[C:5]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 5360545SodiumHCID 53636684HCID 53636684, compound

Product 1

HCID 86735244HCID 86735244, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.23 g. of 2-methyl-3-hydroxy-4-hydroxymethylpyridine-5-acrylic acid, 1 g. of sodium metal, 5 ml. of carbon disulfide, and 75 ml. of absolute ethanol was refluxed for 26 hours. Concentrated hydrochloric acid (3 ml.) was added and the mixture was evaporated to dryness. The residue was extracted with 125 ml. of boiling ethanol and filtered hot. Evaporation of the extract gave a syrup which was crystallized from chloroform-ether to give 2-methyl-3-hydroxy-4-mercaptomethylpyridine-5-acrylic acid hydrochloride, m.p. 227°-228° C.

Workup

  1. additionA mixture of 1.23 g
  2. customthe mixture was evaporated to dryness
  3. extractionThe residue was extracted with 125 ml
  4. filtrationof boiling ethanol and filtered hot
  5. customEvaporation of the extract
  6. customgave a syrup which
  7. customwas crystallized from chloroform-ether

Sources & evidence

ORD record
ord-ebd409ed7ff54281b2c9495ca46f8b76
Source dataset
uspto-grants-1979_03
Patent number
US04144342

Reaction notes

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