Water → HCID 21396810, compound

HRID 1439328Notes

Reaction equation

HRID 1439328 reaction equation
[C:1]([C:3]1[C:4]([O:14][CH2:15][CH2:16][CH3:17])=[N:5][S:6][C:7]=1[NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])#[N:2].[OH2:18].[OH-].[NH4+]>S(=O)(=O)(O)O>[C:1]([C:3]1[C:4]([O:14][CH2:15][CH2:16][CH3:17])=[N:5][S:6][C:7]=1[NH:8][C:9](=[O:13])[CH:10]([CH3:11])[CH3:12])(=[O:18])[NH2:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 21396809HCID 21396809, compound

Product 1

HCID 21396810HCID 21396810, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 8.6 g of N-(4-cyano-3-propoxy-5-isothiazolyl)-2-methylpropanamide, from Example VII, in 20 ml of concentrated sulfuric acid was heated at 50° for 1 hour. Thin-layer chromatographic analysis indicated that the reaction was complete. The reaction mixture was poured into 200 ml of cold water. The solution was neutralized with ammonium hydroxide. The resulting precipitate was collected by filtration. The dried solid was recrystallized from toluene to give 7.7 g of N-(4-carbamoyl-3-propoxy-5-isothiazolyl)-2-methylpropanamide m.p. 153°-154°. The nmr and ir spectra were consistent with the assigned structure.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customThe dried solid was recrystallized from toluene

Sources & evidence

ORD record
ord-fcf8a6070e854ff3870acc1badd3dff8
Source dataset
uspto-grants-1977_11
Patent number
US04059433

Reaction notes

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