Acetic Anhydride → HCID 10388089, compound

HRID 857660Notes

Reaction equation

HRID 857660 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3[N:16]=[CH:15][N:14]=[C:13]([O:17][C:18]4[C:23]5[N:24]=[C:25]([NH2:27])[S:26][C:22]=5[CH:21]=[CH:20][CH:19]=4)[CH:12]=3)=[CH:10][C:4]=2[O:3]1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:28])[CH2:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3[N:16]=[CH:15][N:14]=[C:13]([O:17][C:18]4[C:23]5[N:24]=[C:25]([NH:27][C:29](=[O:31])[CH3:30])[S:26][C:22]=5[CH:21]=[CH:20][CH:19]=4)[CH:12]=3)=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21865279HCID 21865279, compound

Product 1

HCID 10388089HCID 10388089, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a 100-mL, round-bottomed flask containing 4-[6-(2,2-dimethyl-2,3-dihydro-benzofuran-6-yl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine, (Example 133(b)), (0.50 g, 1.3 mmol) was added toluene (7 mL) and acetic anhydride (0.40 mL, 3.8 mmol, Aldrich). The reaction mixture was heated at 85° C. for 2 h. The toluene was removed in vacuum and the resulting orange solid was re-dissolved in dichloromethane (125 mL), washed with water (150 mL), dried over Na2SO4 and concentrated in vacuum. The resulting orange solid was suspended in dichloromethane (100 mL), collected by filtration, and dried under vacuum to obtain the title compound as a white solid. Mp: 224–225° C. MS (ESI, pos. ion.) m/z: 433 (M+1).

Workup

  1. customThe toluene was removed in vacuum
  2. dissolutionthe resulting orange solid was re-dissolved in dichloromethane (125 mL)
  3. washwashed with water (150 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. filtrationcollected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-d3ae2a2becbc43b39739efb6f0897bd6
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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