Hydrochloric Acid → HCID 86735244, compound

HRID 223515Notes

Reaction equation

HRID 223515 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-cf1e9347a6854df8b186540bb19ee68c
Source dataset
uspto-grants-1982_10
Patent number
US04355034

Reaction notes

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