Chloroacetic Acid → HCID 131710350, compound

HRID 1658737Notes

Reaction equation

HRID 1658737 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[S:9])=[CH:3][CH:2]=1.S[C:12]1C=CN=CC=1.ClCC(O)=O>>[CH3:12][O:10][C:8](=[S:9])[CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

4

Reactant 3

HCID 300Chloroacetic AcidHCID 178418431pyridine-4-thiolHCID 178526164HCID 178526164, compound

Product 1

HCID 131710350HCID 131710350, compound

Procedure

It is also known to use 4- or Γ-mercaptopyridine as the starting compound. For instance, in J. Chem. Soc. 1939 873-877, King and Ware described the preparation of 4-pyridylthioacetic acid by treating 4-mercapto-pyridine with ClCH2COOH in a weakly basic medium, while Takahashi et al, as described in Pharm. Bull. (Japan) 2 30-34 (1954), obtain methyl-4-pyridylthioacetate by heating 4-mercaptopyridine for one hour on a water-bath with ClCH2CO2Me. In Gazz. Chim. Ital. 84 584-594 (1954), Musante and Fabbrini mention the preparation of 4-pyridylthioacetic acid by causing 4-mercapto-pyridine to react with ClCH2CONEt2 and treating the resulting 4-(diethylcarbamoylmethylmercapto)pyridine with KOH. In Wiss. Z. Tech. Hochsch. Chem. Leuna-Merseburg 2 187-193 (1959-1960) the preparation of (2-methyl-4-pyridylthio)acetic acid from ClCH2CO2H and 4-mercapto-2-methylpyridine is mentioned, the latter product being obtained by converting 4-nitro-2-methylpyridine-N-oxide into 4-chloro-2-methyl-pyridine and causing this to react with KHS.

Sources & evidence

ORD record
ord-9642558291bc441ea3dbd3062a5026a7
Source dataset
uspto-grants-1976_06
Patent number
US03966741

Reaction notes

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