Hydrochloric Acid → HCID 20341792, compound

HRID 2050129Notes

Reaction equation

HRID 2050129 reaction equation
C([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18](=[O:32])[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:12]([N+:33]([O-:35])=[O:34])[CH:11]=1)(=O)C1C=CC=CC=1.[OH-].[Na+].Cl>CO>[N+:33]([C:12]1[CH:11]=[C:10]([OH:9])[CH:15]=[CH:14][C:13]=1[O:16][CH2:17][C:18](=[O:32])[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([O-:35])=[O:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20341739HCID 20341739, compound

Product 1

HCID 20341792HCID 20341792, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 1 liter of methanol were suspended 275 g of 1-benzoyloxy-3-nitro-4-(dodecylcarbamoylmethoxy)benzene and 50 g of sodium hydroxide were added to the suspension at room temperature under stirring. After stirring for 30 minutes, the reaction solution was poured into 3 liters of ice water to which 150 ml of concentrated hydrochloric acid had been added. Extraction with 3 liters of ethyl acetate was effected and the ethyl acetate layer was washed three times with 3 liters of 5% aqueous sodium bicarbonate solution, dried over sodium sulfate and concentrated. The residual crystal was washed with acetonitrile. The yield was 203 g and the melting point was 150°-151° C. (acetonitrile).

Workup

  1. additionwere added to the suspension at room temperature
  2. stirringAfter stirring for 30 minutes
  3. additionhad been added
  4. extractionExtraction with 3 liters of ethyl acetate
  5. washthe ethyl acetate layer was washed three times with 3 liters of 5% aqueous sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. washThe residual crystal was washed with acetonitrile

Sources & evidence

ORD record
ord-614dffa8c01b46b88f70250300783260
Source dataset
uspto-grants-1980_04
Patent number
US04200466

Reaction notes

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