Acetic Anhydride → HCID 22039040, compound

HRID 1016772Notes

Reaction equation

HRID 1016772 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:7][O:6][CH:5]([C:8]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:9]=2/[C:10](/[NH:13][OH:14])=[N:11]/[H])[O:4][CH2:3]1.[CH2:24]1CCN2C(=NCCC2)C[CH2:25]1.C(OC(=O)C)(=O)C>CN(C=O)C>[CH3:1][C:2]1([CH3:23])[CH2:7][O:6][CH:5]([C:8]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:9]=2[C:10]2[N:11]=[C:24]([CH3:25])[O:14][N:13]=2)[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178506516HCID 178506516, compound

Product 1

HCID 22039040HCID 22039040, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.34 g of (E)- and/or (Z)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-N-hydroxy-4,5-dimethoxy-benzamidine, 1.20 ml of DBU and 0.61 ml of acetic anhydride in 50 ml of DMF was stirred for 1 hr. at room temperature and subsequently for 2 hrs. at 80° C. Subsequently, the DMF was removed in a vacuum and the residue was taken up in ethyl acetate. The ethyl acetate phase was washed with water and saturated NaCl solution and, after removal of the solvent, the residue was purified by column chromatography (CH2Cl2/ethyl acetate). There were obtained 0.43 g of 3-[2-(5,5-dimethyl-[1,3]dioxan-2-yl)-4,5-dimethoxy-phenyl]-5-methyl-[1,2,4]oxadiazole as a white solid; MS: 334 ([M]+).

Workup

  1. waitat room temperature and subsequently for 2 hrs
  2. customat 80° C
  3. customSubsequently, the DMF was removed in a vacuum
  4. washThe ethyl acetate phase was washed with water and saturated NaCl solution
  5. customafter removal of the solvent
  6. customthe residue was purified by column chromatography (CH2Cl2/ethyl acetate)

Sources & evidence

ORD record
ord-72787124d54a4d92b84f9576768179ca
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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