Acetic Anhydride → 1-[N-formyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

HRID 1741416Notes

Reaction equation

HRID 1741416 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][NH:19][CH:20]3[C:28]4[C:23](=[C:24]([O:29][CH3:30])[CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:31](OC(=O)C)(=[O:33])C>C(O)=O>[CH:31]([N:19]([CH:20]1[C:28]2[C:23](=[C:24]([O:29][CH3:30])[CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)[CH2:18][C:9]1[O:10][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1)=[O:33]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 183673131-(4,5-diphenyloxazol-2-yl)methylamino-2,3-dihydro-4-methoxy-1H-indene

Product 1

HCID 183674231-[N-formyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of 1-(4,5-diphenyloxazol-2-yl)methylamino-2,3-dihydro-4-methoxy-1H-indene (0.13 g) in formic acid (5 ml) was added acetic anhydride (1 ml) at 0° C. After being stirred for 5 hours at room temperature, the solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with water, sat. NaHCO3, and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give 1-[N-formyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.12 g). MS (m/z): 425 (M+ +1) NMR (CDCl3, δ): 8.52 (0.25H, s), 8.43 (0.75H, s), 7.60-7.40 (4H, m), 7.38-7.24 (6H, m), 7.18-6.95 (1H, m), 6.78-6.55 (2H, m), 6.18 (0.25H, m), 5.28 (0.75H, m), 4.72 (0.75H, d, J=16.2 Hz), 4.51 (0.75H, d, J=16.2 Hz), 4.12 (0.5H, m), 3.79 (2.25H, s), 3.72 (0.75H, s), 3.20-2.94 (1H, m), 2.92-2.66 (1H, m), 2.62-2.38 (1H, m), 2.35-2.05 (1H, m)

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  3. washThe organic layer was washed with water, sat. NaHCO3, and brine
  4. customThe dried solvent was evaporated in vacuo
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ce0b4e390ada4dd5911696f442ad7b7f
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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