2-Bromomethylnaphthalene → 2-Naphthylmethyl ethanimidothioate hydrobromide

HRID 750755Notes

Reaction equation

HRID 750755 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].[Br:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1>C(Cl)(Cl)Cl>[BrH:5].[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[CH2:6][S:3][C:1](=[NH:4])[CH3:2]

Participants

4

Reactant 2

HCID 703202-BromomethylnaphthaleneHCID 2723949Thioacetamide

Product 1

HCID 221387052-Naphthylmethyl ethanimidothioate hydrobromideYield 78.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thioacetamide (326.0 mg, 4.339 mmol) and 2-bromomethyl-naphthalene (959.0 mg, 4.337 mmol) were placed in a 50 mL round-bottom flask. 20 mL of CHCl3 were added and the mixture was refluxed for 3 h at which time a white precipitate formed. The mixture was cooled and the precipitate collected. The precipitate was washed with 20 mL of CH2Cl2 and placed under vacuum for drying to give 1.01 g of thioacetimidic acid naphthalen-2-ylmethyl ester hydrobromide salt as a fine white powder.

Workup

  1. temperaturethe mixture was refluxed for 3 h at which time a white precipitate
  2. customformed
  3. temperatureThe mixture was cooled
  4. customthe precipitate collected
  5. washThe precipitate was washed with 20 mL of CH2Cl2
  6. customfor drying

Sources & evidence

ORD record
ord-aa40cb0bdfda4a8f9a128849bacec49c
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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