Trimethylaluminum → HCID 18626983, compound

HRID 1860253Notes

Reaction equation

HRID 1860253 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:13](=[O:15])[NH2:14])=[CH:5][C:6]=1[CH2:7][C:8](OCC)=[O:9].C[Al](C)C>ClCCl>[O:9]=[C:8]1[NH:1][C:2]2[S:3][C:4]([C:13]([NH2:14])=[O:15])=[CH:5][C:6]=2[CH2:7]1

Participants

4

Reactant 2

HCID 16682925TrimethylaluminumHCID 69844672HCID 69844672, compound

Product 1

HCID 18626983HCID 18626983, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-amino-5-carbamoylthiophene-3-acetate (500 mg, 2.19 mmol) was dissolved in dry dichloromethane (20 ml) and treated at 0° C. with trimethyl-aluminium (2M in heptane, 3.5 ml, 7.22 mmol). The reaction mixture was allowed to warm slowly to room temperature over 3 hours, cooled to 0° C. and quenched with saturated aqueous ammonium chloride solution. The solution was extracted with ethyl acetate, the organic phase was dried over magnesium sulfate, evaporated to dryness and the residue chromatographed on silica gel using ethyl acetate as eluent to give 210 mg of 5,6-dihydro-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxamide as a pale grey solid. MS(ES): m/e 183 [M+H].

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with saturated aqueous ammonium chloride solution
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. customevaporated to dryness
  6. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-00e29856e28343d299cd5bc6747b417a
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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