Acetic Anhydride → HCID 54317682, compound

HRID 437713Notes

Reaction equation

HRID 437713 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]([CH3:12])([CH3:11])[CH2:8][CH2:9][CH3:10])[C:3]=1[C:13]#[N:14].[CH:15](OCC)(OCC)[O:16][CH2:17][CH3:18].C(OC(=O)C)(=O)C>O1CCOCC1>[C:13]([C:3]1[C:4]([C:7]([CH3:12])([CH3:11])[CH2:8][CH2:9][CH3:10])=[N:5][S:6][C:2]=1[N:1]=[CH:15][O:16][CH2:17][CH3:18])#[N:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 21426747HCID 21426747, compound

Product 1

HCID 54317682HCID 54317682, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 25 g of 5-amino-4-cyano-3-(1,1-dimethylbutyl)isothiazole and 35.6 g of triethyl orthoformate in 200 ml of dioxane was heated under reflux for two hours. To the solution was added 24.5 g of acetic anhydride and the mixture was heated under reflux an additional 20 hours. The mixture wss concentrated under reduced pressure and the residue was distilled in a short path still at 120° under 0.1 mm Hg to give 31.8 g of 4-cyano-3-(1,1-dimethylbutyl)-5-[N-(ethoxymethylene)amino] isothiazole which was dissolved in 125 ml of ethanol, without further purification. The ethanolic solution was placed in a flask equipped with a gas inlet tube and one outlet of which was closed by a small rubber balloon. Dimethylamine gas was passed into the solution until the balloon remained inflated; during the introduction of dimethylamine, the temperature of the mixture increased to 60°. The reaction mixture was concentrated under reduced pressure. The residue was recrystallized from a mixture of diethyl ether (90 parts) and pentane (10 parts) at low temperature to give 26.5 g of N'-[4-cyano-3-(1,1-dimethylbutyl)-5-isothiazolyl]-N,N-dimethylformamidine, m.p. 65°-67°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperatureunder reflux for two hours
  2. temperaturethe mixture was heated
  3. temperatureunder reflux an additional 20 hours
  4. concentrationThe mixture wss concentrated under reduced pressure
  5. distillationthe residue was distilled in a short path still at 120° under 0.1 mm Hg

Sources & evidence

ORD record
ord-b7f0a5667ed448f4a9159d9a4050a2aa
Source dataset
uspto-grants-1977_06
Patent number
US04032322

Reaction notes

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