Thiourea → HCID 86690875, compound

HRID 1465573Notes

Reaction equation

HRID 1465573 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][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:7][C:6]=1[CH3:26])=O.[NH2:27][C:28]([NH2:30])=[S:29]>CCO>[CH3:11][C:10]1[CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:15][CH:14]=2)[CH:7]=[C:6]([CH3:26])[C:5]=1[C:3]1[N:27]=[C:28]([NH2:30])[S:29][CH:2]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690876HCID 86690876, compound

Product 1

HCID 86690875HCID 86690875, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(2,6-dimethyl-4-(4-phenoxyphenoxy)phenyl)ethanone (26-3, 9.53 g, 23.2 mmol) and thiourea (1.76 g, 23.1 mmol) in 95% EtOH (33.1 mL) was heated at reflux for 60 min. The solution was concentrated and added with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and washed with ethyl acetate. The solids were dried under vacuum to give 4-(2,6-dimethyl-4-(4-phenoxyphenoxy)phenyl)thiazol-2-amine (26-4, 9.00 g) as brown solids in 100% yield, which was used directly for the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 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. washwashed with ethyl acetate
  7. customThe solids were dried under vacuum

Sources & evidence

ORD record
ord-67d191c9ce1a45fb87793e82158c60df
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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