Thiourea → HCID 58442504, compound

HRID 1480685Notes

Reaction equation

HRID 1480685 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[C:15]([CH3:17])[C:14]([C:18](=O)[CH2:19]Br)=[C:13]([CH3:22])[CH:12]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[NH2:23][C:24]([NH2:26])=[S:25]>CCO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[C:15]([CH3:17])[C:14]([C:18]4[N:23]=[C:24]([NH2:26])[S:25][CH:19]=4)=[C:13]([CH3:22])[CH:12]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442393HCID 58442393, compound

Product 1

HCID 58442504HCID 58442504, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-(benzo[d][1,3]dioxol-5-yloxy)-2,6-dimethylphenyl)-2-bromoethanone (6.13 g, 16.9 mmol) and thiourea (1.29 g, 16.9 mmol) in 95% EtOH (24.1 mL) was heated at reflux for 90 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-(benzo[d][1,3]dioxol-5-yloxy)-2,6-dimethylphenyl)thiazol-2-amine (5.50 g) as yellow solids in 96% yield: 1H NMR (500 MHz, CDCl3) δ 6.75 (d, J=8.5 Hz, 1H), 6.66 (s, 2H), 6.58 (m, 1H), 6.49 (m, 1H), 6.28 (s, 1H), 5.98 (s, 2H), 5.05 (bs, 2H), 2.13 (s, 6H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 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-0f2b1e9535f34f1f890f555817f5f63d
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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