Hydrochloric Acid → 5-(4-Fluorobenzoyl)-4-methyl-1,3-thiazol-2(3H)-one

HRID 569785Notes

Reaction equation

HRID 569785 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:15][C:16]1[NH:17][C:18](=[O:21])[S:19][CH:20]=1.Cl>ClCC(Cl)(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:20]2[S:19][C:18](=[O:21])[NH:17][C:16]=2[CH3:15])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 678794-Fluorobenzoyl chlorideHCID 2209364-Methyl-1,3-thiazol-2(3H)-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 141522585-(4-Fluorobenzoyl)-4-methyl-1,3-thiazol-2(3H)-oneYield 51.7%

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

4-Fluorobenzoyl chloride (25.3 g, 0.16 mol) was added dropwise to a mixture of aluminum chloride (60 g, 0.45 mol) and 4-methyl-2(3H)-thiazolone (17.3 g, 0.15 mol) in tetrachloroethane (200 ml). After the addition was complete, the mixture was stirred for 5 hours at 90° C. After the mixture cooled to room temperature, 2N hydrochloric acid (200 ml) was added dropwise. The resulting precipitate was collected, washed with water and then with dichloromethane. The solid was then dissolved in ethanol and heated with charcoal. Subsequent recrystalization from ethanol gave the title compound (18.4 g), M.p. 209°-210° C.

Workup

  1. additionAfter the addition
  2. temperatureAfter the mixture cooled to room temperature
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. dissolutionThe solid was then dissolved in ethanol
  6. temperatureheated with charcoal
  7. customSubsequent recrystalization from ethanol

Sources & evidence

ORD record
ord-489eaa690d3e4b8397fd46bb87d1adce
Source dataset
uspto-grants-1988_03
Patent number
US04734422

Reaction notes

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