Ethanol → HCID 21198568, compound

HRID 1066339Notes

Reaction equation

HRID 1066339 reaction equation
[CH2:1]([S:6]([NH:9][C:10](=[O:30])[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[CH:12]=1)(=[O:8])=[O:7])[CH2:2][CH2:3][CH2:4][CH3:5].O1CCCC1.C(O)C.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH2:1]([S:6]([NH:9][C:10](=[O:30])[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[CH:12]=1)(=[O:8])=[O:7])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 21198573HCID 21198573, compound

Product 1

HCID 21198568HCID 21198568, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

N-(n-pentanesulfonyl)-3-(2,4-dichlorobenzylamino)-4-nitrobenzamide (38.9 g) was mixed with 200 ml of tetrahydrofuran, 200 ml of ethanol and 800 ml of water. Sodium hydrosulfite (214.2 g) was added all at once to the mixture with stirring. Immediately, the mixture was placed on an oil bath at 90° C. and refluxed for 40 minutes. The mixture was then cooled down and separated into aqueous and organic layers. The organic layer was concentrated, and water was added to the resulting residue. The precipitate thus formed was separated by filtration, and washed subsequently with water and ethyl acetate. Ethanol (520 ml) was added to the resulting solid, and the mixture was refluxed at 100° C. to dissolve the solid completely. Water (230 ml) was added to the heated solution, and the mixture was cooled with stirring for 1 hour. The resulting crystals were separated through filtration, washed with a solution of ethanol/water (7:3) and dried to give pale-yellow crystals (19.9 g) of N-(n-pentanesulfonyl)-4-amino-3-(2,4-dichlorobenzylamino)benzamide (31).

Workup

  1. customImmediately, the mixture was placed on an oil bath at 90° C.
  2. temperaturerefluxed for 40 minutes
  3. temperatureThe mixture was then cooled down
  4. customseparated into aqueous and organic layers
  5. concentrationThe organic layer was concentrated
  6. additionwater was added to the resulting residue
  7. customThe precipitate thus formed
  8. customwas separated by filtration
  9. washwashed subsequently with water and ethyl acetate
  10. additionEthanol (520 ml) was added to the resulting solid
  11. dissolutionto dissolve the solid completely
  12. additionWater (230 ml) was added to the heated solution
  13. temperaturethe mixture was cooled
  14. stirringwith stirring for 1 hour
  15. customThe resulting crystals were separated through filtration
  16. washwashed with a solution of ethanol/water (7:3)
  17. customdried

Sources & evidence

ORD record
ord-920d486e17104580bacbccf3ad2ac29e
Source dataset
uspto-grants-2001_06
Patent number
US06242474B1

Reaction notes

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