Formaldehyde → Benzothiazoline

HRID 385003Notes

Reaction equation

HRID 385003 reaction equation
[CH2:1]=O.[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10]>O.C(OC(C)C)(C)C>[S:10]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH2:1]1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 87132-Aminothiophenol

Product 1

HCID 96588Benzothiazoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

37% formalin (5.2 mL) was diluted with water (80 mL), and diisopropylether (80 mL) and 2-aminobenzenethiol (7.84 g) were added, and then the mixture was stirred at mom temperature for 30 minutes. The organic layer was separated and the aqueous layer was extracted with diisopropylether. 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 (c).

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with diisopropylether
  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 (c)

Sources & evidence

ORD record
ord-4cda6bdfc23841e0bd7e15558c15bc40
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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