Acetic acid 2-isothiocyanatoethylester → Acetic acid 2-{3-[2-(3,5-dimethyl-phenyl)-1-(5,6,7,8-tetrahydro-naphthalen-1-yl)-ethyl]-thioureido}-ethyl ester

HRID 2039440Notes

Reaction equation

HRID 2039440 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH2:21])[C:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=[CH:13][CH:12]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[N:22]([CH2:25][CH2:26][O:27][C:28](=[O:30])[CH3:29])=[C:23]=[S:24]>C(Cl)(Cl)Cl>[CH3:8][C:6]1[CH:5]=[C:4]([CH2:9][CH:10]([NH:21][C:23](=[S:24])[NH:22][CH2:25][CH2:26][O:27][C:28](=[O:30])[CH3:29])[C:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=[CH:13][CH:12]=2)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 13552411Acetic acid 2-isothiocyanatoethylesterHCID 668873512-(3,5-Dimethylphenyl)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)-ethylamine

Product 1

HCID 86657463Acetic acid 2-{3-[2-(3,5-dimethyl-phenyl)-1-(5,6,7,8-tetrahydro-naphthalen-1-yl)-ethyl]-thioureido}-ethyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(3,5-dimethylphenyl)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)-ethylamine (2.18 g) in 40 ml of chloroform was treated with acetic acid 2-isothiocyanato-ethyl ester (1.13 g) at room temperature and the mixture heated under reflux for 2 hours. After completion of the reaction the solvent was evaporated in vacuo and the residue was purified on silica gel with a gradient of cyclohexan/ethyl acetate. This yielded the title compound in 2.74 g (83%).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 hours
  3. customAfter completion of the reaction the solvent
  4. customwas evaporated in vacuo
  5. customthe residue was purified on silica gel with a gradient of cyclohexan/ethyl acetate

Sources & evidence

ORD record
ord-01c9cc21fc594b3c96592467e1bc6641
Source dataset
uspto-grants-2013_11
Patent number
US08580710B2

Reaction notes

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