1-Phenethylamine → 7-nitro-N-(1-phenylethyl)-1,3-benzothiazol-2-amine

HRID 2235491Notes

Reaction equation

HRID 2235491 reaction equation
Cl[C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:14][CH:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN1CCCC1=O.O>[N+:11]([C:10]1[C:4]2[S:3][C:2]([NH:22][CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:14])=[N:6][C:5]=2[CH:7]=[CH:8][CH:9]=1)([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 74081-PhenethylamineHCID 450777752-Chloro-7-nitrobenzo[d]thiazole

Product 1

HCID 588965417-nitro-N-(1-phenylethyl)-1,3-benzothiazol-2-amineYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 0.160 g (0.75 mmol) of 2-chloro-7-nitro-1,3-benzothiazole in 2 mL of 1-methyl-2-pyrrolidinone (NMP) was added 0.29 μL (2.2 mmol) of racemic α-methylbenzylamine. The reaction was stirred at room temperature for 18 h, diluted with water and extracted with dichloromethane. The organic layer was concentrated in vacuo and purified by flash chromatography eluting with a 25% ethyl acetate/hexanes mixture to give 0.165 g (74%) of the title compound as a light yellow solid which was used without further analysis in the subsequent step.

Workup

  1. extractionextracted with dichloromethane
  2. concentrationThe organic layer was concentrated in vacuo
  3. custompurified by flash chromatography
  4. washeluting with a 25% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-cf90b6e0c7d0415792cb54d625897c2c
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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