Thiourea → HCID 58442494, compound

HRID 1480662Notes

Reaction equation

HRID 1480662 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:6]=1[CH3:18])=O.[NH2:19][C:20]([NH2:22])=[S:21]>CCO>[CH3:18][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=[C:10]([CH3:11])[C:5]=1[C:3]1[N:19]=[C:20]([NH2:22])[S:21][CH:2]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442497HCID 58442497, compound

Product 1

HCID 58442494HCID 58442494, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(3,5-dimethyl-[1,1′-biphenyl]-4-yl)ethanone (2.56 g, 8.44 mmol) and thiourea (0.64 g, 8.44 mmol) in 95% EtOH (12.1 mL) was heated at reflux for 60 min. The solution was concentrated and added with water (50 mL) and saturated aqueous Na2CO3 (1.0 mL). The resultant precipitate was filtered and recrystallized in toluene (10 mL). The solids were filtered and dried under vacuum to give 4-(3,5-dimethyl-[1,1′-biphenyl]-4-yl)thiazol-2-amine (0.66 g) as yellow solids in 28% yield: 1H NMR (500 MHz, CDCl3) δ 7.60 (d, J=1 Hz, 2H), 7.43 (t, J=7.5 Hz, 1H), 7.32 (m, 1H), 7.25 (s, 2H), 6.34 (s, 1H), 5.03 (bs, 2H), 2.24 (s, 6H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (50 mL) and saturated aqueous Na2CO3 (1.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene (10 mL)
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-282f589eb64649a48b92213e74ce1ddf
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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