Pyridine → HCID 20512626, compound

HRID 1902877Notes

Reaction equation

HRID 1902877 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([N:15]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:16][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][CH2:31][CH2:32][CH3:33])=[O:14])[CH:3]=1.N1C=CC=CC=1.[Cl:58][C:59]1[C:64]([Cl:65])=[CH:63][C:62]([S:66](Cl)(=[O:68])=[O:67])=[CH:61][N:60]=1.S(Cl)(Cl)(=O)=O>O1CCCC1>[Cl:58][C:59]1[C:64]([Cl:65])=[CH:63][C:62]([S:66]([NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([OH:12])=[C:4]([C:13]([N:15]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:16][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][CH2:31][CH2:32][CH3:33])=[O:14])[CH:3]=2)(=[O:68])=[O:67])=[CH:61][N:60]=1

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 24648Sulfuryl chlorideHCID 1033282-Naphthalenecarboxamide, 4-amino-1-hydroxy-N,N-dioctadecyl-HCID 47369115,6-dichloropyridine-3-sulfonyl Chloride

Product 1

HCID 20512626HCID 20512626, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 22.5 g (0.0318 mole) 4-amino-1-hydroxy-N,N-dioctadecyl-2-naphthamide and 4.0 g (0.5 mole) pyridine in 300 ml tetrahydrofuran (THF) under nitrogen was stirred at room temperature and a solution of 9.0 g (0.036 mole) 2,3-dichloropyridine-5-sulfonyl chloride in 50 ml THF was added. The mixture was stirred 2 hours at room temperature. A thin-layer Chromogram on silica gel sheets indicated unreacted amine, so an additional 1.0 g of the sulfonyl chloride was added followed by 0.5 ml pyridine and stirring for an additional hour. Since a thin-layer chromotogram indicated no more amine, the mixture was concentrated to a small volume on a rotary evaporator, slurried in water several times with the water layer decanted off each time. The oil was dissolved in ether, water was separated, and the extract was dried with anhydrous Na2SO4. The ether layer was removed to leave a reddish oil which solidified on standing. The oil was extracted several times with boiling acetonitrile to leave a purplish black residue. The extracts were chilled and the precipitate was reextracted; chilling the extracts gave 25.7 g (88 percent) of product as a beige powder with a m.p. 88°-9° C.

Workup

  1. stirringstirring for an additional hour
  2. concentrationthe mixture was concentrated to a small volume on a rotary evaporator
  3. customdecanted off each time
  4. dissolutionThe oil was dissolved in ether
  5. customwater was separated
  6. dry with materialthe extract was dried with anhydrous Na2SO4
  7. customThe ether layer was removed
  8. customto leave a reddish oil which
  9. extractionThe oil was extracted several times with boiling acetonitrile
  10. customto leave a purplish black residue
  11. temperatureThe extracts were chilled
  12. temperaturechilling the extracts

Sources & evidence

ORD record
ord-b40df12d3fb945d6814ba891066e2e87
Source dataset
uspto-grants-1982_12
Patent number
US04366218

Reaction notes

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