Hydrochloric Acid → HCID 10851968, compound

HRID 2228566Notes

Reaction equation

HRID 2228566 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].O1CCOCC1.[OH-].[Na+].Cl>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 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 2807639HCID 2807639, compound

Product 1

HCID 10851968HCID 10851968, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-(4-t-butylbenzoylamino)thiophene-2-carboxylate (9.67 g, 30 mmol), dioxane (75 mL) and 2 M sodium hydroxide (75 mL) was stirred for 16 h. The reaction was acidified to pH 2 with 5 M hydrochloric acid. The mixture was diluted with ethyl acetate and the aqueous layer was extracted with ethyl acetate (3 times). The combined organic layers was magnesium sulfate dried, filtered, and concentrated to afford the title compound as a solid (8.09 g, 89%); NMR(CDCl3) d 1.36(s, 9H), 7.54(d, 2H, J=8.4 Hz), 7.61(d, 1H, J=5.1 Hz), 7.92(d, 2H, J=8.4 Hz), 8.34(d, 1H, J=5.1 Hz), 11.04(s, 1H); MS(FD): 303.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (3 times)
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b21036d5a00f4c8bb2521f10042c08bb
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

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