Acetic Acid → HCID 14033027, compound

HRID 1194737Notes

Reaction equation

HRID 1194737 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[OH-].[Na+].[Cl:9][C:10]([C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([C:24]([Cl:28])=[C:25]([Cl:27])[Cl:26])[CH:23]=1)[CH2:17][N:18]=[N+:19]=[N-:20])=[C:11]([Cl:13])[Cl:12].C(O)(=O)C>C(O)C>[NH2:2][C:1]1[N:18]([CH2:17][C:16]2[CH:21]=[C:22]([C:24]([Cl:28])=[C:25]([Cl:27])[Cl:26])[CH:23]=[C:14]([C:10]([Cl:9])=[C:11]([Cl:12])[Cl:13])[CH:15]=2)[N:19]=[N:20][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7898CyanoacetamideHCID 14798Sodium HydroxideHCID 23036246HCID 23036246, compound

Product 1

HCID 14033027HCID 14033027, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a hot (60° C.) solution of cyanoacetamide (0.692 g) in 25 ml of ethanol, 8.2 ml of a 1N methanolic solution of NaOH was added and the resulting mixture stirred for 20 minutes. 3,5-Di(trichlorovinyl)benzyl azide (1.5 g) was added in one portion and the resulting mixture stirred at 60° C. for 1 hour. The pH of the mixture was adjusted to 6 with acetic acid. The reaction mixture was then concentrated to a reduced volume and diluted with 100 ml of water. The aqueous mixture was extracted with CH2Cl2 (3×100 ml). The combined organic layers were washed with water, dried with MgSO4 and concentrated to give 1.5 g of crude product. This material was chromatographed on silica gel (95:5 CH2Cl2 :CH3OH) to give 890 mg of a solid. Recrystallization from 5 ml of ethanol provided pure triazole, m.p. 167°-169° C.

Workup

  1. stirringthe resulting mixture stirred at 60° C. for 1 hour
  2. concentrationThe reaction mixture was then concentrated to a reduced volume
  3. additiondiluted with 100 ml of water
  4. extractionThe aqueous mixture was extracted with CH2Cl2 (3×100 ml)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customto give 1.5 g of crude product
  9. customThis material was chromatographed on silica gel (95:5 CH2Cl2 :CH3OH)

Sources & evidence

ORD record
ord-10a3bcb3b6684331abdc6fa0f8b7d13b
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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