Tin tetrachloride → 3-Amino-5-cyclopropylethynylthiophene-2-carboxylic acid methyl ester

HRID 72204Notes

Reaction equation

HRID 72204 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH3:6][O:7][C:8]([C:10]1[S:11][C:12]([C:18]#[C:19][CH:20]2[CH2:22][CH2:21]2)=[CH:13][C:14]=1[N+:15]([O-])=O)=[O:9]>C(O)C>[CH3:6][O:7][C:8]([C:10]1[S:11][C:12]([C:18]#[C:19][CH:20]2[CH2:21][CH2:22]2)=[CH:13][C:14]=1[NH2:15])=[O:9]

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 689420965-Cyclopropylethynyl-3-nitrothiophene-2-carboxylic acid methyl ester

Product 1

HCID 689758043-Amino-5-cyclopropylethynylthiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin chloride (11.8 g) was added to a solution of 5-cyclopropylethynyl-3-nitrothiophene-2-carboxylic acid methyl ester (6.26 g) in ethanol (250 ml), and the reaction mixture was heated to reflux for 4 h. The solvent was then removed in vacuo, and the residue was taken up again in ethyl acetate and washed with sat. Rochelle salt solution. The organic phase was dried over sodium sulfate and the solvent was removed in vacuo. The product with the molecular weight of 221.27 (C11H11NO2S) was obtained in this way; MS (ESI): 222 (M+H+).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. customThe solvent was then removed in vacuo
  4. washwashed with sat. Rochelle salt solution
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe product with the molecular weight of 221.27 (C11H11NO2S) was obtained in this way

Sources & evidence

ORD record
ord-ab6d7f67b8be411aa66b359ec94e8dac
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Reaction notes

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