Methylamine → N-methyl 3-(3-trifluoromethylphenyl)-4-amino-5-isothiazolecarboxamide

HRID 67652Notes

Reaction equation

HRID 67652 reaction equation
[CH3:1][NH2:2].[F:3][C:4]([F:23])([F:22])[C:5]1[CH:6]=[C:7]([C:11]2[C:15]([NH2:16])=[C:14]([C:17](OCC)=[O:18])[S:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1>CO>[CH3:1][NH:2][C:17]([C:14]1[S:13][N:12]=[C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:4]([F:23])([F:22])[F:3])[CH:6]=2)[C:15]=1[NH2:16])=[O:18]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13532972Ethyl 3-(3-trifluoromethylphenyl)-4-amino-5-isothiazolecarboxylate

Product 1

HCID 13073259N-methyl 3-(3-trifluoromethylphenyl)-4-amino-5-isothiazolecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One hundred ml. of methanol were saturated with gaseous methyl amine. Two grams of ethyl 3-(3-trifluoromethylphenyl)-4-amino-5-isothiazolecarboxylate were added. The reaction mixture was stirred at ambient temperature for about 30 minutes and was then heated to refluxing temperature for about 30 minutes. TLC indicated some amide had formed. Gaseous methylamine was bubbled through the refluxing reaction mixture for about 4 additional hours, at which time TLC indicated starting material was no longer present. The reaction mixture was poured into an ice-water mixture. N-methyl 3-(3-trifluoromethylphenyl)-4-amino-5-isothiazolecarboxamide formed in the above reaction precipitated and the precipitate collected by filtration. M.P. 113° C. (after vacuum drying). Yield 1.4 g.

Workup

  1. temperaturewas then heated
  2. temperatureto refluxing temperature for about 30 minutes
  3. customhad formed
  4. customGaseous methylamine was bubbled through the refluxing reaction mixture for about 4 additional hours, at which time TLC
  5. additionThe reaction mixture was poured into an ice-water mixture

Sources & evidence

ORD record
ord-03a8439b7c9f4f53a2cf0f7a666d603f
Source dataset
uspto-grants-1982_08
Patent number
US04346094

Reaction notes

Loading…