Formaldehyde → 5-Trifluoromethyl-2,3-dihydro-1,3-benzothiazole

HRID 385158Notes

Reaction equation

HRID 385158 reaction equation
[CH2:1]=O.Cl.[NH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[SH:15]>O.C(OCC)C.C(N(CC)CC)C>[F:14][C:11]([F:12])([F:13])[C:9]1[CH:8]=[CH:7][C:6]2[S:15][CH2:1][NH:4][C:5]=2[CH:10]=1

Participants

6

Reactant 2

HCID 712FormaldehydeHCID 27346782-Amino-4-(trifluoromethyl)benzenethiol hydrochloride

Product 1

HCID 218361675-Trifluoromethyl-2,3-dihydro-1,3-benzothiazole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

37% formalin (0.22 mL) was diluted with water (6 mL), and diethylether (6 mL), triethylamine (0.37 mL) and 2-amino-4-trifluoromethylbenzenethiol hydrochloride (611 mg) were added to the solution, and then the mixture was stirred at room temperature for 30 minutes. The organic layer was separated and the aqueous layer was extracted with diethylether. The organic layers were combined, washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was used for the synthesis of (b).

Workup

  1. additionwere added to the solution
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with diethylether
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was used for the synthesis of (b)

Sources & evidence

ORD record
ord-3af13ecefc214a19a13436999658f132
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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