Water → 4-(4-Chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinic acid

HRID 1768917Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16]C)=[O:15])=[C:12]([S:18][C:19]3[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[N:20]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[C:12]([S:18][C:19]3[N:20]=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([O:25][CH3:26])[N:24]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

16.8 g (0,040 mol) of methyl 4-(4-chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinate was dissolved in 150 ml of dimethylsulfoxide, and 35 ml (0,070 mol) of 2N sodium hydroxide added with stirring at 60° C. After stirring at 60° C. for 30 minutes, the mixture was poured into water, and washed twice with ethyl acetate. The aqueous layer was acidified with 10% hydrochloric acid, and extracted with 500 ml of ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and concentrated. The concentrate was washed with methanol and isopropyl ether to obtain 11.5 g of a white crystal of the aimed product.

Workup

stirringAfter stirring at 60° C. for 30 minutes
washwashed twice with ethyl acetate
extractionextracted with 500 ml of ethyl acetate
washThe extract was washed with water
dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
concentrationconcentrated
washThe concentrate was washed with methanol and isopropyl ether

Sources & evidence

ORD record: ord-5271d012d89d4083b6cdf1a7e0935afe
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380700

Reaction notes

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