4,5-Dichloro-1,2-phenylenediamine → HCID 12521633, compound

HRID 1863173Notes

Reaction equation

HRID 1863173 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.O=[C:12]1[CH2:16][S:15][CH2:14][CH:13]1[C:17](OC)=[O:18]>C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:17](=[O:18])[C:13]3[CH2:14][S:15][CH2:16][C:12]=3[NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 792974,5-Dichloro-1,2-phenylenediamineHCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester

Product 1

HCID 12521633HCID 12521633, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A reaction mixture comprising 106 g. of 4,5-dichloro-o-phenylenediamine and 96 g. of tetrahydro-4-oxo-3-thiophene carboxylic acid, methyl ester in 4 liters of benzene is refluxed for 5 hours and then cooled overnight. The benzene is removed by distillation and replaced by toluene. The mixture is refluxed 2 hours, 10 ml. of water and 0.5 ml. of acetic acid are added and the mixture is refluxed overnight, cooled to room temperature and filtered. The solid is washed with three 100 ml. portions of toluene and air dried giving 6,7-dichloro-1,3,4,9-tetrahydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one.

Workup

  1. temperaturecooled overnight
  2. customThe benzene is removed by distillation
  3. temperatureThe mixture is refluxed 2 hours
  4. additionof acetic acid are added
  5. temperaturethe mixture is refluxed overnight
  6. filtrationfiltered
  7. washThe solid is washed with three 100 ml
  8. dry with materialportions of toluene and air dried

Sources & evidence

ORD record
ord-c1e5bcc0e2224710b7e04fb66ec481a2
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

Loading…