Acetic Acid → HCID 12377875, compound

HRID 236718Notes

Reaction equation

HRID 236718 reaction equation
[C:1]([C:9]1[CH:14]=[C:13](N)[CH:12]=[CH:11][C:10]=1[N:16]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]([C:25]([O:27][CH3:28])=[O:26])=[N:17]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(O)=O.N([O-])=O.[Na+].O.[ClH:38]>>[C:1]([C:9]1[CH:14]=[C:13]([Cl:38])[CH:12]=[CH:11][C:10]=1[N:16]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]([C:25]([O:27][CH3:28])=[O:26])=[N:17]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 962Water2×HCID 12377874HCID 12377874, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 12377875HCID 12377875, compound

Procedure

To a solution of 13.1 g. (34.5 mmol) of the final product of Example 2 in 50 ml. HOAc and 75 ml. of 3 N HCl, stirred at 3°, was added dropwise so as to maintain a temperature of 3°-6°, a solution of 2.50 g. (36.3 mmol) of sodium nitrite in 25 ml. H2O. When the addition was complete, the reaction was stirred at 3° for 20 minutes. A fresh solution of cuprous chloride in concentrated hydrochloric acid (prepared from 27 g. cupric sulfate pentahydrate*) was mixed with an equal volume of water and cooled to 3°. The diazotized solution, which had to be kept cold (<5°) at all times, was slowly poured into the vigorously stirred 5° cuprous chloride solution in several portions, in order to control foaming.

Workup

  1. additionwas added dropwise so as
  2. temperatureto maintain a temperature of 3°-6°
  3. additionWhen the addition
  4. temperaturecooled to 3°
  5. custom(<5°)

Sources & evidence

ORD record
ord-02430053508a49fb9090486fe9818368
Source dataset
uspto-grants-1979_06
Patent number
US04157331

Reaction notes

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