Acetic Anhydride → HCID 22350976, compound

HRID 896617Notes

Reaction equation

HRID 896617 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]1=[N:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.[C:32](OC(=O)C)(=[O:34])[CH3:33].C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[N:6]([CH2:5][CH2:4][CH2:3][NH:2][C:32](=[O:34])[CH3:33])[C:7](=[N:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:8][CH:9]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22351049HCID 22351049, compound

Product 1

HCID 22350976HCID 22350976, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[3-(3-Aminopropyl)-4-(4-bromophenyl)-thiazol-2(3H)-ylidene]aniline hydrochloride (730 mg) obtained in Example 132 and triethylamine (0.77 ml) were dissolved in N,N-dimethylformamide (5 ml), and thereto were added dropwise acetic anhydride in an ice bath under nitrogen atmosphere. The mixture was stirred at the same temperature for 2 hours, and thereto was added a saturated aqueous sodium hydrogen carbonate solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from isopropyl alcohol to give the title compound (580 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-e5c643d0ed314dd8bdcfb536615adcdb
Source dataset
uspto-grants-2005_07
Patent number
US06919361B2

Reaction notes

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