Thiourea → HCID 86690846, compound

HRID 1465544Notes

Reaction equation

HRID 1465544 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][O:22][CH3:23])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[CH3:24])=O.[NH2:25][C:26]([NH2:28])=[S:27]>CCO>[CH3:23][O: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:25]=[C:26]([NH2:28])[S:27][CH:2]=3)=[C:6]([CH3:24])[CH:7]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690847HCID 86690847, compound

Product 1

HCID 86690846HCID 86690846, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-{4-(4-(2-methoxyethoxy)phenoxy)-2,6-dimethylphenyl}ethanone (12-5, 835.6 mg, 2.1 mmol) and thiourea (161.7 mg, 2.1 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 (10.0 mL). The resultant precipitate was filtered and recrystallized in toluene (30 mL). The solids were collected and dried under vacuum to give 4-{4-(4-(2-methoxyethoxy)phenoxy)-2,6-dimethylphenyl}thiazol-2-amine (12-6, 322.2 mg), 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 (10.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene (30 mL)
  7. customThe solids were collected
  8. customdried under vacuum

Sources & evidence

ORD record
ord-a20fb38381b54f3c91e5c765207080a5
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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