1,3-Butanedione, 1-(2-thienyl)- → 1,3-Butanedione, 1-(2-thienyl)-

HRID 1285366Notes

Reaction equation

HRID 1285366 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:11])[CH2:7][C:8](=[O:10])[CH3:9].C([O-])(=O)C.[NH4+:16]>C1(C)C=CC=CC=1>[NH2:16][C:8]([CH3:9])=[CH:7][C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:11].[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:11])[CH2:7][C:8](=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 764531,3-Butanedione, 1-(2-thienyl)-HCID 517165Ammonium Acetate

Product 2

HCID 764531,3-Butanedione, 1-(2-thienyl)-Yield 159.5%HCID 68541850HCID 68541850, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The intermediate 3-amino-1-(2-thienyl)-2-buten-1-one was prepared as follows: A mixture containing 153 g of 1-(2-thienyl)-1,3-butanedione, 176.7 g of ammonium acetate and 1 liter of toluene was azeotroped for five hours and then allowed to cool. The solid that separated from the reaction mixture was collected, washed successively with toluene and ether, and dried in a vacuum oven at 90° C. to yield 122 g of 1-(2-thienyl)-1,3-butanedione, m.p. 167°-171° C. A 10 g sample of this material was dissolved in 300 ml of boiling toluene, the solution treated with decolorizing charcoal and filtered, and the filtrate allowed to cool. The solid that separated was collected and dried in a vacuum oven at 90° C. to yield 5.8 g of 3-amino-1-(2-thienyl)-2-buten-1-one, as off-white needles, m.p. 170°-172° C. The main portion of the product was then dissolved in boiling isopropyl alcohol, the hot solution treated with decolorizing charcoal and filtered, and the filtrate allowed to cool. The solid that crystallized was collected, washed with isopropyl alcohol, dried in a vacuum oven at 80° C. to yield 74.1 g of product melting at 169°-171° C.

Workup

  1. customwas azeotroped for five hours
  2. temperatureto cool
  3. customThe solid that separated from the reaction mixture
  4. customwas collected
  5. washwashed successively with toluene and ether
  6. customdried in a vacuum oven at 90° C.

Sources & evidence

ORD record
ord-565190358233403f86b4d15241cd86f9
Source dataset
uspto-grants-1986_01
Patent number
US04567186

Reaction notes

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