Thionyl Chloride → HCID 19995701, compound

HRID 230981Notes

Reaction equation

HRID 230981 reaction equation
C(S[C:4]1N=C[C:7]([C:10]([Cl:12])=[O:11])=[C:6]([Cl:13])[N:5]=1)C.C(SC1NC(=O)C(C(O)=O)=CN=1)C.P(Cl)(Cl)(Cl)=O.OC1C(C(O)=O)=NC2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1.S(Cl)(Cl)=O>CN(C)C=O>[Cl:13][C:6]1[C:7]([C:10]([Cl:12])=[O:11])=[N:34][C:35]2[C:4](=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:5]=1

Participants

7

Reactant 5

HCID 24386Thionyl ChlorideHCID 24813Phosphorus oxychlorideHCID 23422127HCID 23422127, compoundHCID 54038390HCID 54038390, compoundHCID 178524845HCID 178524845, compound

Product 1

HCID 19995701HCID 19995701, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

o-Halogeno-(hetero-)aryl-carboxylic acid halides which can be employed in the process according to the invention, and processes for their preparation, are known. Thus, for example, J. Am. Chem. Soc. 40,233 (1908) describes the preparation of 2-ethylmercapto-6-chloropyrimidine-5-carboxylic acid chloride by reacting 2-ethylmercapto-4-oxo-3,4-dihydropyrimidine-5-carboxylic acid with phosphorus oxychloride. The reaction of 2-hydroxy-quinoxaline-3-carboxylic acid with thionyl chloride in the presence of a catalytic amount of dimethylformamide to give 2-chloroquinoxaline-3-carboxylic acid chloride is described in Arch. Pharm. 306, 401 (1973). The reaction 4-chloronicotinic acid with thionyl chloride under reflex to give 4-chloronicotinic acid chloride is described in J. Chem. Soc. (C), 1966, 1816.

Workup

  1. customaccording to the invention, and processes for their preparation

Sources & evidence

ORD record
ord-82c6d95473f64bd8a91dfc69809f3c41
Source dataset
uspto-grants-1989_07
Patent number
USRE032975

Reaction notes

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