Acetic Anhydride → HCID 178476613, compound

HRID 847179Notes

Reaction equation

HRID 847179 reaction equation
C([N:3]=[C:4]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:5][C@@H:6]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[C@H:7]1[OH:20])#N.[C:28](OC(=O)C)(=[O:30])[CH3:29]>N1C=CC=CC=1>[C:28]([O:20][C@H:7]1[C@H:6]([NH:5][C:4]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[NH:3])[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]1([CH3:18])[CH3:19])(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178431174HCID 178431174, compound

Product 1

HCID 178476613HCID 178476613, compoundYield 112.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The solution of the title compound from Example 3 (2.52 g, 6.98 mmoles) and acetic anhydride (1.0 g, 9.8 mmoles) in pyridine (25 ml) was stirred for 60 hours at room temperature. The crude reaction mixture was partitioned between ethyl acetate and 5% aqueous hydrogen chloride. The organic layer was washed with distilled water, saturated sodium hydrogen carbonate solution, saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was recovered under vacuum to obtain 2.97 g of a white solid. The crude reaction product was recrystallized from ethanol in two crops to obtain 2.24 g of the title compound as a pure white solid, m.p. 239°-240° C. 1H NMR (DMSO-d6) δ 9.36 (s, 1H), 7.63 (m, 3H), 7.35 (m, 2H), 7.20 (m, 3H), 6.97 (d, J=8.80 Hz, 1H), 5.23 (m, 2H), 2.17 (s, 3H), 1.34 (s, 3H), 1.25 (s, 3H). 13C NMR (DMSO-d6) δ 169.69, 158.69, 155.75, 136.95, 132.94, 132.66, 129.03, 125.28, 124.25, 123.79, 118.86, 118.09, 116.62, 103.31, 78.43, 72.07, 49.49, 25.85, 20.67, 19.54.

Workup

  1. customThe crude reaction mixture
  2. customwas partitioned between ethyl acetate and 5% aqueous hydrogen chloride
  3. washThe organic layer was washed with distilled water, saturated sodium hydrogen carbonate solution, saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was recovered under vacuum

Sources & evidence

ORD record
ord-27064af08dbd42af96006e860d1965b7
Source dataset
uspto-grants-1992_08
Patent number
US05140031

Reaction notes

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