Acetic Anhydride → HCID 10433404, compound

HRID 859026Notes

Reaction equation

HRID 859026 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([O:14][C:15]3[C:20]4[N:21]=[C:22]([NH2:24])[S:23][C:19]=4[CH:18]=[CH:17][CH:16]=3)[CH:9]=2)=[CH:4][CH:3]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([O:14][C:15]3[C:20]4[N:21]=[C:22]([NH:24][C:25](=[O:27])[CH3:26])[S:23][C:19]=4[CH:18]=[CH:17][CH:16]=3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21865137HCID 21865137, compound

Product 1

HCID 10433404HCID 10433404, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a 50 mL, round-bottomed flask containing 4-[6-(4-bromo-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine, (Example 129(c)), (0.050 g, 0.13 mmol) was added anhydrous toluene (3 mL) and acetic anhydride (0.010 mL, 0.39 mmol, Aldrich). The mixture was heated at 90° C. and the progress of the reaction was monitored by TLC (developed in 50% EtOAc/hexanes). After reaching completion, the reaction mixture was allowed to cool to room temperature, the white precipitate was collected by filtration, washed with MeOH (5 mL), and dried under vacuum to obtain the title compound as a white solid. Mp: 271–272° C. MS (ESI, pos. ion.) m/z: 441 (M+1).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe white precipitate was collected by filtration
  3. washwashed with MeOH (5 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e28c108f5bc54e2eb75d902223361945
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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