3-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester → HCID 12521637, compound

HRID 1606452Notes

Reaction equation

HRID 1606452 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([Cl:10])=[CH:5][C:4]=1[NH2:11].O=[C:13]1[CH2:17][S:16][CH2:15][CH:14]1[C:18]([O:20]C)=O>C1(C)C=CC=CC=1>[Cl:9][C:7]1[C:6]([Cl:10])=[CH:5][C:4]2[NH:11][C:18](=[O:20])[C:14]3[CH2:15][S:16][CH2:17][C:13]=3[N:2]([CH3:1])[C:3]=2[CH:8]=1

Participants

4

Reactant 2

HCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl esterHCID 30163614,5-Dichloro-2-(methylamino)aniline

Product 1

HCID 12521637HCID 12521637, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.7 g. of N-methyl-4,5-dichloro-o-phenylenediamine and 1.85 g. of methyl tetrahydro-4-oxo-3-thiophenecarboxylate in 150 ml. of toluene is heated under reflux for 3 hours during which 100 ml. of distillate is collected in a Dean-Stark trap. The solution is cooled and the solid which separates is recrystallized from ethyl acetate to give yellow crystals, m.p. 281°-283°C.

Workup

  1. temperatureunder reflux for 3 hours during which 100 ml
  2. distillationof distillate is collected in a Dean-Stark trap
  3. temperatureThe solution is cooled
  4. customthe solid which separates is recrystallized from ethyl acetate
  5. customto give yellow crystals, m.p. 281°-283°C.

Sources & evidence

ORD record
ord-b505d091930948e7b2e4035e6a227496
Source dataset
uspto-grants-1976_04
Patent number
US03953430

Reaction notes

Loading…