Thiourea → HCID 86690859, compound

HRID 1465555Notes

Reaction equation

HRID 1465555 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]([O:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[CH3:23])=O.[NH2:24][C:25]([NH2:27])=[S:26]>CCO>[CH:20]([O: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:24]=[C:25]([NH2:27])[S:26][CH:2]=3)=[C:6]([CH3:23])[CH:7]=2)=[CH:14][CH:15]=1)([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690860HCID 86690860, compound

Product 1

HCID 86690859HCID 86690859, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-(4-isopropoxyphenoxy)-2,6-dimethylphenyl)ethanone (16-5, 2.57 g, 6.8 mmol) and thiourea (0.60 g, 7.8 mmol) in 95% EtOH (30.0 mL) was heated at reflux for 4.0 h. The solution was concentrated and added with water (10 mL) and saturated aqueous Na2CO3 (1.0 mL). The resultant precipitate was filtered and washed with hot water. The solids were filtered and dried under vacuum to give 4-(4-(4-isopropoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-amine (16-6, 1.48 g) as yellow solids in 61% yield: 1H NMR (500 MHz, DMSO-d6) 6.94 (m, 6 H), 6.62 (s, 2 H), 6.33 (s, 1 H), 4.54 (t, J=6.0 Hz, 1 H), 2.05 (s, 6 H), 1.26 (s, 3 H), 1.25 (s, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4.0 h
  3. concentrationThe solution was concentrated
  4. additionadded with water (10 mL) and saturated aqueous Na2CO3 (1.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. washwashed with hot water
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-5d7d39223af242be9641285cf4749206
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

Loading…