Hydrochloric Acid → HCID 10851968, compound

HRID 842374Notes

Reaction equation

HRID 842374 reaction equation
[C:1]([C:5]1[CH:22]=[CH:21][C:8]([C:9]([NH:11][C:12]2[CH:16]=[CH:15][S:14][C:13]=2[C:17]([O:19]C)=[O:18])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>O1CCOCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:22]=[CH:21][C:8]([C:9]([NH:11][C:12]2[CH:16]=[CH:15][S:14][C:13]=2[C:17]([OH:19])=[O:18])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2807639HCID 2807639, compound

Product 1

HCID 10851968HCID 10851968, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of methyl 3-[(4-t-butylbenzoyl)amino]-2-thiophenecarboxylate (9.67 g, 30 mmol) in dioxane (75 mL) was added 2 M sodium hydroxide (75 mL). After 16 h, the mixture was acidified to pH 2 with 5 M hydrochloric acid, then diluted with ethyl acetate. The phases were separated and the aqueous layer was extracted a total of 3 times with ethyl acetate. The combined ethyl acetate fractions were dried over magnesium sulfate, filtered, and the solvent was removed in vacuo to afford the product (8.09 g, 89% yield).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted a total of 3 times with ethyl acetate
  3. dry with materialThe combined ethyl acetate fractions were dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-387906b602d8415fad400ed5f7c9224f
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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