Benzyl Bromide → S-benzylthiobenzimidate hydrobromide

HRID 8927

Reaction equation

HRID 8927 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([Br:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[BrH:17].[CH2:10]([S:8][C:1](=[NH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 683563Thiobenzamide

Product 1

HCID 12624654S-benzylthiobenzimidate hydrobromideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of thiobenzamide (0.307 g, 2.24 mmol) in CH2Cl2 (11 mL) was added benzyl bromide (0.26 mL, 2.19 mmol) and the resultant solution was heated to reflux for 2 h. The mixture was cooled to room temperature and concentrated under reduced pressure. The resultant yellow solid was dried under vacuum to provide S-benzylthiobenzimidate hydrobromide (0.573 g, 85%). 1H NMR (DMSO-d6) δ 4.76 (s, 2H), 7.34–7.44 (m, 3H), 7.51–7.54 (m, 2H), 7.61–7.66 (m, 2H), 7.78–7.83 (m, 1H), 7.88–7.91 (m, 2H), 11.92 (br s, 1H).

Workup

  1. temperatureto reflux for 2 h
  2. concentrationconcentrated under reduced pressure
  3. customThe resultant yellow solid was dried under vacuum

Sources & evidence

ORD record
ord-8753c4924bb442778d438b5dc7c0fe64
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Linked notes

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