Thiourea → HCID 86690843, compound

HRID 1465541Notes

Reaction equation

HRID 1465541 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([S:12][C:13]2[CH:18]=[N:17][CH:16]=[CH:15][N:14]=2)=[CH:7][C:6]=1[CH3:19])=O.[NH2:20][C:21]([NH2:23])=[S:22]>CCO>[CH3:19][C:6]1[CH:7]=[C:8]([S:12][C:13]2[CH:18]=[N:17][CH:16]=[CH:15][N:14]=2)[CH:9]=[C:10]([CH3:11])[C:5]=1[C:3]1[N:20]=[C:21]([NH2:23])[S:22][CH:2]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690844HCID 86690844, compound

Product 1

HCID 86690843HCID 86690843, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(2,6-dimethyl-4-(pyrazin-2-ylthio)phenyl)ethanone (11-4, 4.00 g, 11.9 mmol) and thiourea (902.9 mg, 11.9 mmol) in 95% EtOH (15 mL) was heated at reflux for 16 hr. The solution was concentrated and added with water (50 mL) and saturated aqueous Na2CO3 (10.0 mL). The resultant precipitate was filtered and recrystallized in toluene (30 mL). The solids were filtered and dried under vacuum to give 4-(2,6-dimethyl-4-(pyrazin-2-ylthio)phenyl)thiazol-2-amine (11-5, 1.56 g) as yellow solids in 42% yield: 1H NMR (500 MHz, CDCl3) δ 8.43 (s, 1 H), 8.36 (s, 1 H), 8.31 (s, 1 H), 7.47 (s, 2 H), 6.34 (s, 1 H), 2.24 (s, 6 H). ESI-MS: m/z 315.2 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hr
  3. concentrationThe solution was concentrated
  4. additionadded with water (50 mL) and saturated aqueous Na2CO3 (10.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene (30 mL)
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-6aab21be28fe4405a65c121ae16492a8
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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