Thiourea → HCID 86690868, compound

HRID 1465566Notes

Reaction equation

HRID 1465566 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[CH3:25])=O.[NH2:26][C:27]([NH2:29])=[S:28]>CCO>[CH3:24][O:23][CH2:22][CH2:21][CH2:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]([C:3]3[N:26]=[C:27]([NH2:29])[S:28][CH:2]=3)=[C:6]([CH3:25])[CH:7]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690869HCID 86690869, compound

Product 1

HCID 86690868HCID 86690868, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-{4-(4-(3-methoxypropoxy)phenoxy)-2,6-dimethylphenyl}ethanone (21-4, 0.34 g, 0.82 mmol) and thiourea (0.07 g, 0.96 mmol) in 95% EtOH (5.0 mL) was heated at reflux for 2.0 h. The solution was concentrated and added with water (10 mL) and saturated aqueous Na2CO3 (1.0 mL). The resultant precipitate was filtered and washed with hot water. The solids were filtered and dried under vacuum to give 4-{4-(4-(3-methoxypropoxy)phenoxy)-2,6-dimethylphenyl}thiazol-2-amine (21-5, 0.28 g) as yellow solids in 90% yield, which was used directly for the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.0 h
  3. concentrationThe solution was concentrated
  4. additionadded with water (10 mL) and saturated aqueous Na2CO3 (1.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. washwashed with hot water
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-8a31bf9fa503413ea10c75a03ea153c8
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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