Acetic Anhydride → HCID 14882844, compound

HRID 359090Notes

Reaction equation

HRID 359090 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1>[C:23]([N:8]([CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1)[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14882805HCID 14882805, compound

Product 1

HCID 14882844HCID 14882844, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 4-[3-[N-(4-chlorophenyl)amino]propoxy]benzoate (1.2 g) was dissolved in pyridine (15 ml), and acetic anhydride (0.71 ml) was added thereto. The mixture was stirred at room temperature for 14 hours and concentrated under reduced pressure. The residue was separated into layers by adding ethyl acetate and diluted hydrochloric acid. The organic layer was washed successively with-water, saturated aqueous sodium bicarbonate solution and water, and concentrated under reduced pressure to give the desired product (1.38 g). mp. 68°-69° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was separated into layers
  3. additionby adding ethyl acetate and diluted hydrochloric acid
  4. washThe organic layer was washed successively with-water, saturated aqueous sodium bicarbonate solution and water
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1c0171336c548c2a7de66a69b22e314
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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