Acetic Anhydride → HCID 15550192, compound

HRID 992670Notes

Reaction equation

HRID 992670 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[C:6]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:7]=1[NH2:8])#[N:2].[C:18](OC(=O)C)(=[O:20])[CH3:19].C(OCC)(=O)C.C([O-])(O)=O.[Na+]>C(O)(=O)C.O>[C:1]([C:3]1[S:4][CH:5]=[C:6]([C:9]2[C:10]([CH3:17])=[CH:11][C:12]([CH3:16])=[CH:13][C:14]=2[CH3:15])[C:7]=1[NH:8][C:18](=[O:20])[CH3:19])#[N:2]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 15550191HCID 15550191, compound

Product 1

HCID 15550192HCID 15550192, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of intermediate 3 (6.0 g) in acetic acid (6 ml) was added acetic anhydride (5 g). The reaction mixture was stirred for 1 hour at 110° C. After cooling, the crude mixture was poured into a mixture of ethyl acetate (400 ml), water (600 ml) and saturated NaHCO3 (200 ml). The organid layer was rinsed with water and concetrated. The residue was purified by column chromatography on SiO2 (gradient; hexane: diethyl ether=2:1 to hexane:ethyl acetate=1:1) to give N-[2-cyano-4-(2,4,6-trimethylpenyl)-thiophen-3-yl]-acetamide (intermediate 4).

Workup

  1. temperatureAfter cooling
  2. washThe organid layer was rinsed with water
  3. customThe residue was purified by column chromatography on SiO2 (gradient; hexane: diethyl ether=2:1 to hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-454eafad29cf4dd49404e889584f760a
Source dataset
uspto-grants-2002_10
Patent number
US06469166B2

Reaction notes

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