Hydrochloric Acid → HCID 67812940, compound

HRID 2401366Notes

Reaction equation

HRID 2401366 reaction equation
CON(C)[C:4]([C:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][CH:7]=1)=[O:5].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1.Cl>C1COCC1.C(OCC)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:4]([C:6]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][CH:7]=2)=[O:5])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 84557435HCID 84557435, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 67812940HCID 67812940, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−40° C.) solution of N-methoxy-N,4,5-trimethylthiophene-3-carboxamide (1.77 g, 8.88 mmol) in THF (10 mL) was slowly added (over 10 min) a solution of 4-chlorophenylmagnesium bromide (17 mL, 17.00 mmol, 1 M) in diethyl ether. The reaction mixture was allowed to gradually warm to room temperature and age for several hours. To the mixture was added 1 N HCl and the aqueous layer was extracted with EtOAc (2×). The combined organic layer was washed with saturated NaHCO3, water, dried over Na2SO4, and concentrated to give an oil. The resultant oil was purified on Biotage system (gradient elution 1% EtOAc:99% Hexanes to 4% EtOAc:96% Hexanes) to give the titled compound as white solids (2.00 g, 7.96 mmol, 90% yield). LC/MS m/z 251 [M+H]+.

Workup

  1. waitage for several hours
  2. extractionthe aqueous layer was extracted with EtOAc (2×)
  3. washThe combined organic layer was washed with saturated NaHCO3, water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe resultant oil was purified on Biotage system (gradient elution 1% EtOAc:99% Hexanes to 4% EtOAc:96% Hexanes)

Sources & evidence

ORD record
ord-4ec54758bac0427f8e83933fc7ea66e8
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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