HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → 2-[(4,6-Dimethoxypyrimidin-2-yl)thio]-6-methylbenzoic acid

HRID 1650079
Notes
Print preview

Reaction equation

HRID 1650079 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[N:17]=[C:16](S(C)(=O)=O)[N:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[N:17]=[C:16]([S:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=2[C:4]([OH:6])=[O:5])[N:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 126128092-Mercapto-6-methylbenzoic acid

Product 1

HCID 33868902-[(4,6-Dimethoxypyrimidin-2-yl)thio]-6-methylbenzoic acidYield 12.2%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

Then, 3.6 g of 2-mercapto-6-methylbenzoic acid, 4.7 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 3.5 g of unhydrous potassium carbonate were dissolved in 20 ml of dimethylformamide, and then the mixture was stirred at from 110 to 120° C. for one hour. The reaction solution was poured into a large amount of water, and concentrated hydrochloric acid was added thereto. Then, the mixture was extracted with chloroform. The chloroform layer was washed with water and dried, and then the solvent was distilled off under reduced pressure. The crude crystals were purified by column chromatography by using a developing solvent of hexane/ethyl acetate and recrystallized from ethyl acetate to obtain 0.8 g of 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-methylbenzoic acid as white powder. Melting point: 131°-132° C.

Workup

  1. additionwas added
  2. extractionThen, the mixture was extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe crude crystals were purified by column chromatography
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f4abf0cb65524ae692f2e69e60bbc2ba
Source dataset
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04923501

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes