Sodium Chloride → HCID 20437380, compound

HRID 1980165Notes

Reaction equation

HRID 1980165 reaction equation
[CH2:1]([NH:17][C:18]1[CH:38]=[CH:37][C:21]([C:22]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=2)(=[O:27])=[O:26])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Cl-].[Na+]>[Pd].O1CCCC1>[CH2:1]([NH:17][C:18]1[CH:38]=[CH:37][C:21]([C:22]([NH:24][S:25](=[O:26])([C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)=[O:27])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 20437378HCID 20437378, compound

Product 1

HCID 20437380HCID 20437380, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of p-hexadecylamino-N-(p-nitrophenylsulfonyl)benzamide in 150 ml. of tetrahydrofuran is hydrogenated in the presence of 0.9 g. of 10% palladium on carbon catalyst at approximately 50 lbs. for 22 hours. The mixture is filtered through a bed of diatomaceous earth and the filtrate is evaporated to an incompletely reduced, off-white solid as indicated by thin layer chromatography on silica gel using chloroform:ethyl acetate:acetic acid 95:4:1 as solvent. The product is hydrogenated again in 80 ml. of dimethylformamide plus 1.0 g. of 10% palladium on carbon catalyst for 18 hours at 50 lbs. pressure. The mixture is filtered through a bed of diatomaceous earth and the filtrate is diluted with 500 ml. of eater to give a suspension which is coagulated by the addition of 50 g. of sodium chloride. The mixture is filtered, the product is washed thoroughly with water and dried in a dessicator to give 8.35 g. of product which is a single spot of TLC. The product is crystallized twice from ethyl acetate and dried in an Abderhalden pistol at 65° C. to provide 6.45 g. of pale tan crystals, melting point 193°-196° C.

Workup

  1. filtrationThe mixture is filtered through a bed of diatomaceous earth
  2. customthe filtrate is evaporated to
  3. waitof 10% palladium on carbon catalyst for 18 hours at 50 lbs
  4. filtrationThe mixture is filtered through a bed of diatomaceous earth
  5. additionthe filtrate is diluted with 500 ml
  6. customof eater to give a suspension which
  7. additionis coagulated by the addition of 50 g
  8. filtrationThe mixture is filtered
  9. washthe product is washed thoroughly with water
  10. customdried in a dessicator
  11. customto give 8.35 g
  12. customThe product is crystallized twice from ethyl acetate
  13. customdried in an Abderhalden pistol at 65° C.
  14. customto provide 6.45 g

Sources & evidence

ORD record
ord-cd67a70be760459fa3ea51ac9d6d6da7
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Reaction notes

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