Water → Ethyl 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 1406840Notes

Reaction equation

HRID 1406840 reaction equation
Cl.[NH2:2]O.C([O-])=O.[Na+].[CH2:8]([O:10][C:11]([C:13]1[S:17][C:16]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH:25]=O)[CH:19]=2)=[N:15][C:14]=1[CH3:27])=[O:12])[CH3:9].O>C(O)=O>[CH2:8]([O:10][C:11]([C:13]1[S:17][C:16]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([C:25]#[N:2])[CH:19]=2)=[N:15][C:14]=1[CH3:27])=[O:12])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 1354047235-Thiazolecarboxylic acid, 2-(3-formyl-4-hydroxyphenyl)-4-methyl-, ethyl ester

Product 1

HCID 135627703Ethyl 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Hydroxylamine hydrochloride (35.82 g, 0.515 mol) and sodium formate (46.73 g, 0.687 mol) were added to a solution of ethyl-2-(3-formyl-4-hydroxyphenyl)-4-methyl-5-thiazole carboxylate (100 g, 0.343 mol) in formic acid (anhydrous, 300 mL) and the reaction mixture was heated to a temperature of about 100° C. for about 8 hours. After completion of reaction, the reaction mixture was cooled to about 40° C. and water was added to it. The reaction mixture was cooled to about 25° C. and stirred for about 1 hour. The solid obtained was filtered, washed with water and dried. The solid was then dissolved in acetone at about 50° C. and water was added slowly over a period of about 30 minutes. The mixture was cooled to about 25° C. and again stirred for about 1 hour. The solid thus obtained was filtered, washed with acetone:water (1:1) mixture and dried to obtain the title product. (Yield: 85 g, 85.9%)

Workup

  1. customAfter completion of reaction
  2. temperaturethe reaction mixture was cooled to about 40° C.
  3. temperatureThe reaction mixture was cooled to about 25° C.
  4. customThe solid obtained
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried
  8. dissolutionThe solid was then dissolved in acetone at about 50° C.
  9. additionwater was added slowly over a period of about 30 minutes
  10. temperatureThe mixture was cooled to about 25° C.
  11. stirringagain stirred for about 1 hour
  12. customThe solid thus obtained
  13. filtrationwas filtered
  14. washwashed with acetone:water (1:1) mixture
  15. customdried

Sources & evidence

ORD record
ord-bd9ee626fe064ba2846f4b800a6ada63
Source dataset
uspto-grants-2014_12
Patent number
US08916713B2

Reaction notes

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