Water → HCID 20154310, compound

HRID 2413894Notes

Reaction equation

HRID 2413894 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.[Cl:11][CH2:12][C:13](Cl)=[O:14].[Cl-].[Al+3].[Cl-].[Cl-].O>ClCCl>[Cl:11][CH2:12][C:13]([C:8]1[S:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:10][CH:9]=1)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 20154304HCID 20154304, compound

Product 1

HCID 20154310HCID 20154310, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 23 g of 2-(4-chlorobutyl)thiophene and 17.9 g of chloroacetyl chloride in 250 ml of dichloromethane is added a small portion of 21 g of aluminum chloride under cooling at 0°-5° C. and with stirring. After stirring under cooling with ice for 2 hours, the resultant mixture is poured into water and the organic layer is separated. The water layer is extracted with chloroform and the extract is combined with the organic layer. The combined organic layer is washed with water and dried over magnesium sulfate. The solvent is distilled off under reduced pressure to give 30 g of 2-chloroacetyl-5-(4-chlorobutyl)thiophene as a brown oil. To a solution of the oil in 300 ml of ethanol is added 11 g of thiourea, and refluxed on a water bath for 2 hours. After the solvent is concentrated under reduced pressure, water is added to the residue and the precipitated crystalline hydrochloride is collected by filtration. To a suspension of the crystals in a mixture of water and ethyl acetate is added sodium hydrogencarbonate until the mixture is made alkaline. The organic layer is separated, washed with water and dried over magnesium sulfate. After the is distilled off under reduced pressure, the residue is recrystallized from ethanol to give 2-amino-4-[5-(4-chlorobutyl)-2-thienyl] thiazole as pale yellow crystals, melting at 99°-100° C.

Workup

  1. temperatureunder cooling at 0°-5° C.
  2. stirringAfter stirring
  3. temperatureunder cooling with ice for 2 hours
  4. customthe organic layer is separated
  5. extractionThe water layer is extracted with chloroform
  6. washThe combined organic layer is washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-d7f0a1b74cbe4b0eac293c3cefd54504
Source dataset
uspto-grants-1988_01
Patent number
US04720493

Reaction notes

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