Phosphorus oxychloride → HCID 20467843, compound

HRID 1903043Notes

Reaction equation

HRID 1903043 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=O)[CH3:2].P(Cl)(Cl)([Cl:27])=O>C1(C)C=CC=CC=1>[ClH:27].[CH3:2][C:1]1[C:22]2[CH:21]=[CH:20][C:19]([O:23][CH3:24])=[CH:18][C:17]=2[O:16][C:15]2[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12832027Ethyl 3-acetamido-4-(3-methoxyphenoxy)benzoate

Product 1

HCID 20467843HCID 20467843, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 8.3 g of ethyl 3-acetylamino-4-(3-methoxyphenoxy)-benzoate and 15.4 g of phosphorus oxychloride and 50 ml of dried toluene was refluxed for 3 hours. The mixture was then cooled and the precipitating crystal was filtered and washed with ethyl acetate to give 8.2 g of ethyl 11-methyl-3-methoxydibenz[b,f][1,4]oxazepine-8-carboxylate hydrochloride. The product was neutralized with ammonia water and extracted with ethyl acetate. After concentrating the extract, ethanol was added to the residue and the precipitating crystal was recrystallized from ethanol to give 6.9 g of ethyl 11-methyl-3-methoxydibenz[b,f][1,4]oxazepine-8-carboxylate as a colorless acicular crystal.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe mixture was then cooled
  3. filtrationthe precipitating crystal was filtered
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-4ffe155787194f10b01431c193545037
Source dataset
uspto-grants-1984_03
Patent number
US04435391

Reaction notes

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