Pyridine → HCID 70198733, compound

HRID 342454Notes

Reaction equation

HRID 342454 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[C:12]2[O:13][C:14]([CH3:18])=[C:15]([CH2:16][OH:17])[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:5].[C:24](OC(=O)C)(=[O:26])[CH3:25].N1C=CC=CC=1>ClCCl>[C:24]([O:17][CH2:16][C:15]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:2]=3[Cl:1])[C:12]=2[O:13][C:14]=1[CH3:18])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 70196657HCID 70196657, compound

Product 1

HCID 70198733HCID 70198733, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-(2,6-dichlorobenzoylamino)-3-hydroxymethyl-2-methylbenzo[b]furan (123 mg), acetic anhydride (43 mg) and pyridine (48 mg) in dichloromethane (5 ml) was refluxed for 2 hours. The reaction mixture was washed with 1N-hydrochloric acid, brine and aqueous saturated sodium bicarbonate, dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from diethyl ether to give 3-acetoxymethyl-7-(2,6-dichlorobenzoylamino)-2-methylbenzo[b]furan (115 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. washThe reaction mixture was washed with 1N-hydrochloric acid, brine and aqueous saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-9d488147209b4e16a0010c078be97dbf
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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