Thiourea → HCID 58442504, compound

HRID 1465627Notes

Reaction equation

HRID 1465627 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 20 in 96% yield: 1H NMR (500 MHz, CDCl3) δ 6.75 (d, J=8.5 Hz, 1 H), 6.66 (s, 2 H), 6.58 (m, 1 H), 6.49 (m, 1 H), 6.28 (s, 1 H), 5.98 (s, 2 H), 5.05 (s, 2 H), 2.13 (s, 6 H).

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-11d9c6f9ff66487cad6188f92fd133f0
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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