Acetic Anhydride → HCID 12148628, compound

HRID 2415812Notes

Reaction equation

HRID 2415812 reaction equation
[C:1]1([CH:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:16](OC(N)C)=[CH:17][CH:18]=[CH:19][C:20]=53)=[CH:13][CH:12]=[CH:11][C:10]=4[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[C:31](=[O:33])[CH3:32])(=O)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:1]1([CH:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:16]([O:9][CH2:8][CH2:7][NH:21][C:31](=[O:33])[CH3:32])=[CH:17][CH:18]=[CH:19][C:20]=53)=[CH:13][CH:12]=[CH:11][C:10]=4[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 22336338HCID 22336338, compound

Product 1

HCID 12148628HCID 12148628, compoundYield 141.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of [(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]ethanamine (0.58 g, 1.68 mmol) in DMF (10 mL) is added acetic anhydride (0.17 g, 1.68 mmol) and DMAP (0.01 g, 0.082 mmol). The mixture is heated at 85° C. for 45 min, then partitioned between water and ether. The organic layer is washed twice with water, dried over magnesium sulfate and concentrated. Column chromatography (70 g silica gel) using CH2Cl2/acetone (80/20) as eluent gave 0.46 g (71%) of N-{2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]ethyl}acetamide.

Workup

  1. custompartitioned between water and ether
  2. washThe organic layer is washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-77fd6e37c25245e595cefd392797a153
Source dataset
uspto-grants-2004_11
Patent number
US06821970B2

Reaction notes

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