Acetic Anhydride → HCID 22643590, compound

HRID 29052Notes

Reaction equation

HRID 29052 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:17][O:18][C:19]=2[CH3:20])=[CH:11][CH:10]=1)(=[O:8])=[O:7])=[O:4].C(N(CC)CC)C.[C:34](OC(=O)C)(=[O:36])[CH3:35]>C(#N)C>[C:34]([NH:1][CH2:2][C:3]([NH:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:17][O:18][C:19]=2[CH3:20])=[CH:13][CH:14]=1)(=[O:8])=[O:7])=[O:4])(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22643561HCID 22643561, compound

Product 1

HCID 22643590HCID 22643590, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 2-amino-N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]acetamide (Example 79)(4.08 g, 10.9 mmol) was mixed in acetonitrile at room temperature. Triethylamine (3.03 g, 30.0 mmol) and acetic anhydride (1.23 g, 12.1 mmol) were added and the heterogeneous solution was stirred for 2 hours. The solution was vacuum filtered through a pad of diatomaceous earth and solvent was removed at reduced pressure. Water was added and the solution was stirred for 30 minutes. White crystals formed, were collected by vacuum filtration and dried to afford the desired product as a white solid (3.25 g, 78%): mp 218.2-219.3° C. 1H NMR (CD3OD/300 MHz) 8.01 (d, 2H, J=8.2 Hz), 7.42-7.36 (m, 7H), 3.85 (s, 2H), 2.50 (s, 3H), 1.95 (s, 3H). FABLRMS m/z 414 (M+H). Anal. Calc'd for C20H19N3O5S: C, 58.10; H, 4.63; N, 10.16. Found: C, 58.18; H, 4.66; N, 10.14.

Workup

  1. filtrationfiltered through a pad of diatomaceous earth and solvent
  2. customwas removed at reduced pressure
  3. additionWater was added
  4. stirringthe solution was stirred for 30 minutes
  5. customWhite crystals formed
  6. filtrationwere collected by vacuum filtration
  7. customdried

Sources & evidence

ORD record
ord-f79bf9176904496c97db9347cc6b7c64
Source dataset
uspto-grants-2008_09
Patent number
US07420061B2

Reaction notes

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