Acetic Anhydride → HCID 15550192, compound

HRID 1383305Notes

Reaction equation

HRID 1383305 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 organic layer was rinsed with water and concentrated. 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-trimethylphenyl)-thiophen-3-yl]-acetamide (intermediate 4).

Workup

  1. temperatureAfter cooling
  2. washThe organic layer was rinsed with water
  3. concentrationconcentrated
  4. 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-ab644ce55c20444a8f40826f14934042
Source dataset
uspto-grants-2001_07
Patent number
US06255310B1

Reaction notes

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