Thionyl Chloride → 2-(3-Chlorophenoxy)nicotinoyl chloride

HRID 1679798Notes

Reaction equation

HRID 1679798 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9].S(Cl)([Cl:20])=O>Cl.C(N(CC)CC)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([Cl:20])=[O:9]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 122026412-(3-Chlorophenoxy)nicotinic acid

Product 1

HCID 226121122-(3-Chlorophenoxy)nicotinoyl chlorideYield 98.3%

Reagents, catalysts & solvents 2

HCID 11130Triethylamine hydrochlorideCatalystHCID 6212ChloroformSolvent

Procedure

In the same manner as in Example 1(a), 22.1 grams 2(3-chlorophenoxy)nicotinic acid, 13.0 grams (0.1 mole) thionyl chloride, 0.5 grams triethylamine hydrochloride and 200 milliliters chloroform were combined to yield 23.2 grams (98.3% of theoretical) of 2(3-chlorophenoxy) nicotinoyl chloride, m.p. 72°-74° C. The structure was confirmed by mass spectrometry.

Sources & evidence

ORD record
ord-f9b4be72bfa94ab384dd0b7bf118a7ef
Source dataset
uspto-grants-1981_06
Patent number
US04270946

Reaction notes

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