Butylamine → N-n-butyl-3-methyl-5-isothiazolecarboxylic acid amide

HRID 2255487Notes

Reaction equation

HRID 2255487 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[S:4][N:3]=1.C(N(CC)CC)C.[CH2:17]([NH2:21])[CH2:18][CH2:19][CH3:20]>C(OCC)(=O)C>[CH2:17]([NH:21][C:7]([C:5]1[S:4][N:3]=[C:2]([CH3:1])[CH:6]=1)=[O:9])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 8471TriethylamineHCID 2740923-Methyl-1,2-thiazole-5-carboxylic acid

Product 1

HCID 54219434N-n-butyl-3-methyl-5-isothiazolecarboxylic acid amide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-5-isothiazolecarboxylic acid (2.3 g) was dissolved in 40 ml of ethyl acetate. After 2 g of triethylamine were added, the resultant mixture was cooled over an ice-water bath and, at 5°-10° C., 1.5 g of n-butylamine were gradually added dropwise. After completion of the dropwise addition, stirring was continued for 30 minutes. The reaction mixture was washed successively with an aqueous solution of sodium hydrogencarbonate and then with water. After dried over sodium sulfate, the solvent was distilled off so that 2.60 g of N-n-butyl-3-methyl-5-isothiazolecarboxylic acid amide were obtained as an oil.

Workup

  1. additionAfter completion of the dropwise addition
  2. washThe reaction mixture was washed successively with an aqueous solution of sodium hydrogencarbonate
  3. dry with materialAfter dried over sodium sulfate
  4. distillationthe solvent was distilled off so that 2.60 g of N-n-butyl-3-methyl-5-isothiazolecarboxylic acid amide
  5. customwere obtained as an oil

Sources & evidence

ORD record
ord-d47183f2e5b3454a9a311f81fb228e31
Source dataset
uspto-grants-1993_08
Patent number
US05240951

Reaction notes

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