Acetic Anhydride → HCID 14372570, compound

HRID 1086046Notes

Reaction equation

HRID 1086046 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:19][CH2:20][CH2:21][NH2:22])[CH:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>C(Cl)Cl>[C:23]([NH:22][CH2:21][CH2:20][O:19][C:4]1[CH:3]=[C:2]([NH2:1])[C:17]([Cl:18])=[CH:16][C:5]=1[C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14372569HCID 14372569, compound

Product 1

HCID 14372570HCID 14372570, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-2-(2-aminoethoxy)-5-chloro-N-[2-(diethylamino)ethyl]benzamide (780 mg, 2.4 mmoles) (prepared in Example 47) in methylene chloride was added acetic anhydride (245 mg, 2.4 mmoles) and the mixture stirred for 30 minutes. This was concentrated in vacuo and the residue was partitioned between methylene chloride and sodium bicarbonate solution. The organic phase was concentrated and the residue flash-chromatographed on silica using methylene chloride:methanol:ammonia (100:4:0.5) solvent system. The appropriate fractions were combined and concentrated in vacuo. The residue was recrystallized from methylene chloride-ether to give 445 mg of the title compound as a white solid, mp. 143°-145° C.

Workup

  1. concentrationThis was concentrated in vacuo
  2. customthe residue was partitioned between methylene chloride and sodium bicarbonate solution
  3. concentrationThe organic phase was concentrated
  4. customthe residue flash-chromatographed on silica
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from methylene chloride-ether

Sources & evidence

ORD record
ord-ea88771b7c03408090f766aa6d1592bf
Source dataset
uspto-grants-1991_04
Patent number
US05011992

Reaction notes

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