p-(8-Cyclohexyloctyl)aminobenzoyl chloride hydrochloride → p-(8-cyclohexyloctylamino)-N-(phenylsulfonyl)benzamide

HRID 903420Notes

Reaction equation

HRID 903420 reaction equation
Cl.[CH:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:26]1([S:32]([NH2:35])(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Na]>CC(N(C)C)=O>[CH:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([NH:35][S:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:34])=[O:33])=[O:22])=[CH:19][CH:18]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 20475769p-(8-Cyclohexyloctyl)aminobenzoyl chloride hydrochlorideHCID 24194900Benzenesulfonamide sodium

Product 1

HCID 20475809p-(8-cyclohexyloctylamino)-N-(phenylsulfonyl)benzamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To the resulting oily residue of p-(8-cyclohexyloctyl)aminobenzoyl chloride hydrochloride is added, in one portion, the previously prepared mixture of sodium benzenesulfonamide in dimethylacetamide. The mixture is stirred for 30 minutes, without cooling, and is then filtered through a bed of diatomaceous earth. The filtrate is poured into 2 l. of water, and 250 ml. of saturated sodium chloride solution is added to coagulate the precipitate. The mixture is filtered and the product is washed with water and partially air dried. The product is dissolved in methylene chloride, the mixture is filtered through diatomaceous earth, and brine is added to break the emulsion. The layers are separated, the organic phase is dried over anhydrous sodium sulfate and filtered through a bed of 300 g. of hydrous magnesium silicate. The product is eluted with an additional 3 l. of methylene chloride. The first approx. 1 l. of filtrate is set aside and the remainder is evaporated to dryness. The residue is crystallized three times from toluene to yield the product.

Workup

  1. temperaturewithout cooling
  2. filtrationis then filtered through a bed of diatomaceous earth
  3. additionThe filtrate is poured into 2 l
  4. additionof saturated sodium chloride solution is added
  5. filtrationThe mixture is filtered
  6. washthe product is washed with water and partially air
  7. customdried
  8. dissolutionThe product is dissolved in methylene chloride
  9. filtrationthe mixture is filtered through diatomaceous earth, and brine
  10. additionis added
  11. customThe layers are separated
  12. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  13. filtrationfiltered through a bed of 300 g
  14. washThe product is eluted with an additional 3 l
  15. customthe remainder is evaporated to dryness
  16. customThe residue is crystallized three times from toluene
  17. customto yield the product

Sources & evidence

ORD record
ord-e409bb4a133d4f9b8ee256abd72ccb5a
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

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