Hydrochloric Acid → HCID 19025316, compound

HRID 1033152Notes

Reaction equation

HRID 1033152 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[O:4].Cl.[N:18]([O-])=[O:19].[Na+].C(=O)(O)[O-].[Na+]>O>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[N:18]=[O:19])[N:9]([CH2:10][CH3:11])[CH2:12][CH3:13])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 19025317Methyl [3-(diethylamino)phenyl]carbamateHCID 23668193Sodium Nitrite

Product 1

HCID 19025316HCID 19025316, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

While stirring a mixture of 6.0 g of 3-(methoxycarbonylamino)-N,N-diethylaniline, 10 ml of water, and 2.0 ml of concentrated hydrochloric acid at 0° C, 2.0 g of sodium nitrite was added to the mixture. When the first crystals were deposited in the mixture, 50 ml of water was further added to the mixture followed by stirring for 30 minutes. Thereafter, the reaction mixture obtained was poured into 300 ml of water followed by stirring well, neutralized by the addition of sodium bicarbonate, and extracted with ethyl acetate. After washing with water, the extract was dried by Glauber's salt and the solvent was distilled off using an evaporator to provide a yellow-green oily product. The crude product was purified by silica gel chromatography to provide 6.7 g (yield: 98%) of a product as a green solid.

Workup

  1. additionwas further added to the mixture
  2. stirringby stirring for 30 minutes
  3. customThereafter, the reaction mixture obtained
  4. stirringby stirring well
  5. extractionextracted with ethyl acetate
  6. washAfter washing with water
  7. dry with materialthe extract was dried by Glauber's salt
  8. distillationthe solvent was distilled off
  9. customan evaporator
  10. customto provide a yellow-green oily product
  11. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a10094613b1f4ed4b3168465a7285c51
Source dataset
uspto-grants-1994_05
Patent number
US05310634

Reaction notes

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