Pyridine → HCID 20437382, compound

HRID 1733505Notes

Reaction equation

HRID 1733505 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([NH2:6])(=[O:5])=[O:4].N1C=CC=CC=1.Cl.[CH2:16]([NH:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(Cl)Cl>[CH2:16]([NH:32][C:33]1[CH:34]=[CH:35][C:36]([C:37]([NH:6][S:3]([C:2]([F:8])([F:7])[F:1])(=[O:5])=[O:4])=[O:38])=[CH:40][CH:41]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 79001TrifluoromethylsulfonamideHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 20437382HCID 20437382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.25 g. of trifluoromethanesulfonamide in 35 ml. of pyridine was treated with 3.5 g. of 4-(hexadecylamino)benzoyl chloride hydrochloride in methylene chloride at 10°-15° C. and then stirred under reflux for 3 hours. Evaporation afforded a gum which was stirred with 150 ml. of H2O and extracted with three 50 ml. portions of CHCl3. The extracts were combined, dried (MgsO4), and evaporated to yield a white solid. Crystallization from ether-acetone gave 2.0 g. of product, melting point 172°-174° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customEvaporation
  3. customafforded a gum which
  4. extractionof H2O and extracted with three 50 ml
  5. customdried (MgsO4)
  6. customevaporated
  7. customto yield a white solid
  8. customCrystallization from ether-acetone
  9. customgave 2.0 g

Sources & evidence

ORD record
ord-1f87624b28ab4420bacd8f81b0e3eeac
Source dataset
uspto-grants-1980_12
Patent number
US04242273

Reaction notes

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