Hydrochloric Acid → HCID 20031676, compound

HRID 1980271Notes

Reaction equation

HRID 1980271 reaction equation
[CH3:1][O:2][C:3]([CH:5]([N:7]([C:16](=[O:20])[CH2:17][O:18][CH3:19])[C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:15])[CH3:6])=[O:4].Cl.N([O-])=O.[Na+].[N-:26]=[N+:27]=[N-].[Na+]>O.CCOCC>[CH3:1][O:2][C:3]([CH:5]([N:7]([C:16](=[O:20])[CH2:17][O:18][CH3:19])[C:8]1[C:13]([N:14]=[N+:26]=[N-:27])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:15])[CH3:6])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 14157300HCID 14157300, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20031676HCID 20031676, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

10.0 g of N-(1'-methoxycarbonyl-ethyl)-N-methoxyacetyl-2-methyl-6-aminoaniline were stirred up with 75 g of ice and 15 ml of conc. hydrochloric acid at 0° to 5° C. until a clear solution was formed. At 0° to 5° C. were then added dropwise, within 10 minutes, 2.5 g of sodium nitrite dissolved in 10 ml of water. The reddish-brown solution was stirred for a further 30 minutes at the above temperature, and 100 ml of ether were subsequently added. There was thereupon added dropwise at 0° to 5° C., within 15 minutes, a solution of 2.5 g of sodium azide in 10 ml of water, and the temperature was allowed to rise in the course of 30 minutes to room temperature. The reaction mixture was extracted with ether; the organic phase was then washed with sodium hydrogen carbonate/water, dried with magnesium sulfate, and the solvent was evaporated off. The resulting oil was dried at 40° C. in vacuo; nD26 :1.5396. nD28.5 :1.5389.

Workup

  1. customwas formed
  2. additionAt 0° to 5° C. were then added dropwise, within 10 minutes
  3. additionwere subsequently added
  4. additionThere was thereupon added dropwise at 0° to 5° C., within 15 minutes
  5. extractionThe reaction mixture was extracted with ether
  6. washthe organic phase was then washed with sodium hydrogen carbonate/water
  7. dry with materialdried with magnesium sulfate
  8. customthe solvent was evaporated off
  9. customThe resulting oil was dried at 40° C. in vacuo

Sources & evidence

ORD record
ord-781a1625453b4b2cadc5c6394ef5037a
Source dataset
uspto-grants-1985_04
Patent number
US04508731

Reaction notes

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