1-[2-(3,5-Dimethylphenyl)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)-ethyl]-3-(2-hydroxyethyl)-thiourea → (4,5-Dihydrothiazol-2-yl)-[2-(3,5-dimethylphenyl)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)-ethyl]amine

HRID 2039442Notes

Reaction equation

HRID 2039442 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:21][C:22]([NH:24][CH2:25][CH2:26]O)=[S:23])[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>Cl>[S:23]1[CH2:26][CH2:25][N:24]=[C:22]1[NH:21][CH:10]([C:11]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[CH:14]=[CH:13][CH:12]=1)[CH2:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=1

Participants

3

Reactant 1

HCID 866574621-[2-(3,5-Dimethylphenyl)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)-ethyl]-3-(2-hydroxyethyl)-thiourea

Product 1

HCID 58427944(4,5-Dihydrothiazol-2-yl)-[2-(3,5-dimethylphenyl)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)-ethyl]amineYield 88.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of the above 1-[2-(3,5-dimethylphenyl)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)-ethyl]-3-(2-hydroxyethyl)-thiourea (1.21 g) and concentrated hydrochloric acid (20 ml) was heated under reflux for 2 hours. The hydrochloric acid phase was decanted carefully and the remainder dissolved in ethyl acetate and washed three times with potassium carbonate solution (5 wt % in water), three times with water and dried over sodium sulphate. The solvent was removed by evaporation and the remainder triturated with a solution of light petrol ether/ethyl acetate (10/1) and the precipitate separated by filtration to yield the product C.2 as an off-white solid (1.02 g)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe hydrochloric acid phase was decanted carefully
  4. dissolutionthe remainder dissolved in ethyl acetate
  5. washwashed three times with potassium carbonate solution (5 wt % in water), three times with water
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was removed by evaporation
  8. customthe remainder triturated with a solution of light petrol ether/ethyl acetate (10/1)
  9. customthe precipitate separated by filtration

Sources & evidence

ORD record
ord-a7d210efc6384f6d9942d98f8599fd68
Source dataset
uspto-grants-2013_11
Patent number
US08580710B2

Reaction notes

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