Water → HCID 86690814, compound

HRID 1465514Notes

Reaction equation

HRID 1465514 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([C:15]3[N:16]=[C:17]([NH2:20])[S:18][CH:19]=3)=[C:10]([CH3:21])[CH:9]=2)=[CH:5][CH:4]=1.[C:24]([O-])(=[O:26])[CH3:25].[Na+].O>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH3:21])[C:11]([C:15]3[N:16]=[C:17]([NH:20][C:24](=[O:26])[CH3:25])[S:18][CH:19]=3)=[C:12]([CH3:14])[CH:13]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 58442480HCID 58442480, compound

Product 1

HCID 86690814HCID 86690814, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 4-(4-(4-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-amine (2-1, 500 mg, 1.5 mmol) in acetic anhydride (2.0 mL) was added sodium acetate (125.7 mg, 1.5 mmol). The reaction was stirred at room temperature for 1.0 h. The solution was added with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4(s), and concentrated under reduced pressure to give N-{4-(4-(4-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-yl}acetamide (2-2, 465 mg) as yellow oil in 82% yield: 1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 6.96-7.03 (m, 5 H), 6.64 (s, 2 H), 3.75 (s, 3 H), 2.15 (s, 3 H), 2.01 (s, 6 H). ESI-MS: m/z 368.9 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4(s)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-75ce5769eb0144ba8c61cccf0467fdc0
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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