Hydrochloric Acid → 2-[2-(2,6-dichloroanilino)-4-oxo-1,3-thiazol-5-ylidene]acetic acid

HRID 987560Notes

Reaction equation

HRID 987560 reaction equation
C[O:2][C:3](=[O:20])[CH:4]=[C:5]1[S:9][C:8]([NH:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[N:7][C:6]1=[O:19].[OH-].[Na+].Cl>C1COCC1>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[NH:10][C:8]1[S:9][C:5](=[CH:4][C:3]([OH:20])=[O:2])[C:6](=[O:19])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178499652HCID 178499652, compound

Product 1

HCID 1785252812-[2-(2,6-dichloroanilino)-4-oxo-1,3-thiazol-5-ylidene]acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A reaction mixture of [2-(2,6-dichloro-phenylamino)-4-oxo-4H-thiazol-5-ylidene]-acetic acid methyl ester (3 g, Example 1), NaOH (1N in H2O, 30 mL), THF (20 mL) was heated to 40° C. and stirred for 48 hours. The mixture was acidified to PH=1 by adding 10% aqueous HCl. Then the mixture was extracted with ethyl acetate (25 mL×3). The organic extracts were dried over MgSO4, filtered, concentrated, and dried under vacuum to yield the desired product as a white solid.

Workup

  1. extractionThen the mixture was extracted with ethyl acetate (25 mL×3)
  2. dry with materialThe organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2793e79a969a40a68effe82c347cce08
Source dataset
uspto-grants-2003_10
Patent number
US06632831B2

Reaction notes

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