Benzylamine → HCID 178509283, compound

HRID 57244

Reaction equation

HRID 57244 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[C:13](SC)SC)[C:11]#[N:12].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O.[NH2:27][NH2:28]>C(O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:12])=[N:27][NH:28][C:13]=1[NH:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 24654Hydrazine hydrate (1:1)HCID 28077272-Benzothiazol-2-yl-3,3-bis-methylsulfanylacrylonitrile

Product 1

HCID 178509283HCID 178509283, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-benzothiazol-2-yl-3,3-bismethylsulfanylacrylonitrile (200 mg, 0.73 mmol) and benzylamine (160 mg, 1.5 mmol) in 50 mL of ethanol was heated to reflux for 90 minutes. Hydrazine hydrate (35 μL, 1.0 mmol) was then added to the reaction mixture. The solution was heated to reflux until the reaction was complete as determined by TLC analysis. The reaction solution was allowed to cool to room temperature and the title compound (124 mg) was isolated by filtration, washed with ethanol and dried under high vacuum. MS (m/z, ES+): 322 (M+1, 100%); 1H NMR (300 MHz, ppm, DMSO-d6): δμ11.32 (br s, 1/3H), 10.89 (s, br., 2/3H), 7.98 (d, 3J=7.7 Hz, 1H), 7.82 (d, 3J=8.0 Hz, 1H), 7.41-7.28 (m, 6H), 7.22 (m, 1H), 6.15 (br s, 9/10H), 4.95 (br s, 1/10H), 4.48 (d, 3J=4.7 Hz, 1H). Yield=53%.

Workup

  1. temperatureto reflux for 90 minutes
  2. temperatureThe solution was heated
  3. temperatureto reflux until the reaction

Sources & evidence

ORD record
ord-b9c15dfee0ca4b36b171547a69834048
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Linked notes

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