2,6-Dichloro-1,4-benzenediamine → HCID 13059653, compound

HRID 1164280Notes

Reaction equation

HRID 1164280 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH2:10].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)[CH:16]=O.CO[CH:25](OC)[N:26]([CH3:28])[CH3:27]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:16][C:15]2[CH:14]=[C:13]([O:12][CH3:11])[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=2)[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]=[CH:25][N:26]([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 118602,6-Dichloro-1,4-benzenediamineHCID 78373Dimethylformamide dimethyl acetalHCID 817473,5-Dimethoxybenzaldehyde

Product 1

HCID 13059653HCID 13059653, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 5.3 g. of 2,6-dichloro-p-phenylenediamine and 4.98 g. of 3,5-dimethoxybenzaldehyde in 100 ml. of ethanol is heated on a steam bath, solution occurs, followed by crystallization. Warming is continued on the steam bath for 16 hours. The reaction mixture is cooled, 50 ml. of glacial acetic acid and 500 mg. of platinum oxide are added and the mixture is hydrogenated in a Parr apparatus at 40 p.s.i. for 15 minutes. The mixture is filtered and washed with ethanol, then the combined filtrate and washings are evaporated to dryness. The residue is treated with 200 ml. of saturated sodium carbonate then is extracted twice with 200 ml. of ethyl acetate. The combined extract is evaporated to dryness. The residue is dissolved in methanol and the solution is cooled at 5° C. to provide crystals. The crystals are collected by filtration and washed with methanol to give 7.8 g. of product. This product is heated at reflux with 20 ml. of N,N-dimethylformamide dimethylacetal for 18 hours. The resulting solution is evaporated to an amber syrup. The syrup is treated with ether/hexane to crystallize 7.1 g. of the product of the Example as colorless needles, m.p. 124°-125° C.

Workup

  1. additionA mixture of 5.3 g
  2. customfollowed by crystallization
  3. temperatureWarming
  4. temperatureThe reaction mixture is cooled
  5. additionof platinum oxide are added
  6. waitfor 15 minutes
  7. filtrationThe mixture is filtered
  8. washwashed with ethanol
  9. customthe combined filtrate and washings are evaporated to dryness
  10. additionThe residue is treated with 200 ml
  11. extractionof saturated sodium carbonate then is extracted twice with 200 ml
  12. extractionThe combined extract
  13. customis evaporated to dryness
  14. dissolutionThe residue is dissolved in methanol
  15. customto provide crystals
  16. filtrationThe crystals are collected by filtration
  17. washwashed with methanol
  18. customto give 7.8 g
  19. temperatureThis product is heated
  20. temperatureat reflux with 20 ml
  21. customThe resulting solution is evaporated to an amber syrup
  22. additionThe syrup is treated with ether/hexane
  23. customto crystallize 7.1 g

Sources & evidence

ORD record
ord-cd83d2e24b514016a2a67a12577726ca
Source dataset
uspto-grants-1983_01
Patent number
US04368335

Reaction notes

Loading…