2-Chloro-1,1,1-triethoxyethane → 2-(Chloromethyl)-5-(trifluoromethyl)-1,3-benzothiazole

HRID 1253347Notes

Reaction equation

HRID 1253347 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[SH:13].[Cl:14][CH2:15][C:16](OCC)(OCC)OCC>C(O)C>[Cl:14][CH2:15][C:16]1[S:13][C:4]2[CH:5]=[CH:6][C:7]([C:9]([F:10])([F:11])[F:12])=[CH:8][C:3]=2[N:2]=1

Participants

4

Reactant 2

HCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 27346782-Amino-4-(trifluoromethyl)benzenethiol hydrochloride

Product 1

HCID 142042052-(Chloromethyl)-5-(trifluoromethyl)-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-amino-4-trifluoromethylthiophenol hydrochloride (30.0 g) in ethanol (125 ml) was added 2-chloro-1,1,1-triethoxyethane (31.0 g). The mixture was heated for 1 hour at 60° C. The solution was concentrated to remove excess ethanol and the resulting material was extracted with ether (500 ml). The organic extract was washed successively with 10% HCl (20 ml), water (100 ml), 10% sodium bicarbonate solution and water (100 ml), and then evaporated to obtain an amber colored oil, which crystallized upon standing at room temperature (28.9 g; m.p. 52° C.).

Workup

  1. concentrationThe solution was concentrated
  2. customto remove excess ethanol
  3. extractionthe resulting material was extracted with ether (500 ml)
  4. extractionThe organic extract
  5. washwas washed successively with 10% HCl (20 ml), water (100 ml), 10% sodium bicarbonate solution and water (100 ml)
  6. customevaporated
  7. customto obtain an amber colored oil, which
  8. customcrystallized
  9. customupon standing at room temperature

Sources & evidence

ORD record
ord-a0e26934030546cf9b0f1d6dc0610931
Source dataset
uspto-grants-1988_05
Patent number
US04748280

Reaction notes

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