HCID 86639528, compound → HCID 24894132, compound

HRID 1689609Notes

Reaction equation

HRID 1689609 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:19][C:20]([NH:22][CH2:23][CH2:24]O)=[S:21])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=2[CH3:18])[CH:5]=[C:6]([CH3:8])[CH:7]=1>Cl>[S:21]1[CH2:24][CH2:23][N:22]=[C:20]1[NH:19][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[CH3:18])[CH2:9][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

3

Reactant 1

HCID 86639528HCID 86639528, compound

Product 1

HCID 24894132HCID 24894132, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of the above 1-[2-(3,5-Dimethyl-phenyl)-1-(2,3-dimethyl-phenyl)-ethyl]-3-(2-hydroxy-ethyl)-thiourea (94.7 g) and concentrated hydrochloric acid (700 ml) was heated under reflux for 2 hours. The hydrochloric acid phase was decanted carefully and the remainder dissolved in ethyl acetate and thoroughly 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 titurated with a solution of light petrol ether/ethyl acetate (20/1), filtrated to yield the product (4,5-dihydro-thiazol-2-yl)-[2-(3,5-dimethyl-phenyl)-1-(2,3-dimethyl-phenyl)-ethyl]-amine [specific compound example C.33 of table C] as an off-white solid (67.1 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. washthoroughly washed 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. filtrationfiltrated

Sources & evidence

ORD record
ord-85d5216c9c724f4886116031a7b66a35
Source dataset
uspto-grants-2012_04
Patent number
US08153560B2

Reaction notes

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