Thiourea → HCID 58442439, compound

HRID 1465639Notes

Reaction equation

HRID 1465639 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]([CH2:19][CH3:20])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[CH3:21])=O.[NH2:22][C:23]([NH2:25])=[S:24]>CCO>[CH2:19]([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:22]=[C:23]([NH2:25])[S:24][CH:2]=3)=[C:6]([CH3:21])[CH:7]=2)=[CH:14][CH:15]=1)[CH3:20]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442381HCID 58442381, compound

Product 1

HCID 58442439HCID 58442439, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-(4-ethylphenoxy)-2,6-dimethylphenyl)ethanone (7.70 g, 2212 mmol) and thiourea (1.69 g, 22.2 mmol) in 95% EtOH (31.7 mL) was heated at reflux for 180 min. The solution was concentrated and added with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene. The solids were filtered and dried under vacuum to give 4-(4-(4-ethylphenoxy)-2,6-dimethylphenyl)thiazol-2-amine (6.30 g) as yellow solids in 88% yield: 1H NMR (500 MHz, CDCl3) δ 7.18 (d, J=7.5 Hz, 2 H), 6.95 (d, J=8.5, 2 H), 6.71 (s, 2 H), 6.29 (s, 1H), 5.45 (bs, 2 H), 2.64 (q, J=7.5 Hz, 2 H), 2.14 (s, 6 H), 1.25 (t, J=8.0 Hz, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 180 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-dfdaf9f743974ef7a398c349388aed32
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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