2-Naphthalenecarboxamide, 4-amino-1-hydroxy-N,N-dioctadecyl- → HCID 20493239, compound

HRID 851535Notes

Reaction equation

HRID 851535 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.[C:52]([CH2:54][CH2:55][S:56]([C:59]1[CH:64]=[CH:63][C:62]([S:65](Cl)(=[O:67])=[O:66])=[CH:61][CH:60]=1)(=[O:58])=[O:57])#[N:53]>N1C=CC=CC=1>[C:52]([CH2:54][CH2:55][S:56]([C:59]1[CH:64]=[CH:63][C:62]([S:65]([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:66])=[O:67])=[CH:61][CH:60]=1)(=[O:58])=[O:57])#[N:53]

Participants

4

Reactant 2

HCID 1033282-Naphthalenecarboxamide, 4-amino-1-hydroxy-N,N-dioctadecyl-HCID 20493237HCID 20493237, compound

Product 1

HCID 20493239HCID 20493239, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-amino-1-hydroxy-N,N-dioctadecyl-2-naphthamide (U.S. Pat. No. 4,135,929) (0.03 mol) in 450 ml of degassed pyridine was cooled to 5° to 10° C. and 8.8 g (0.03 mol) of 4-(2-cyanoethylsulfonyl)benzenesulfonyl chloride was added scoopwise at 0° to 5° C. The mixture was stirred for one hour at this temperature and was warmed to 20° to 25° C. and held for one hour. The reaction mixture was drowned in 2 liters of ice and water, filtered, reslurried in water and dried. The product was recrystallized from hexane to give 18 g (62 percent) of a tan solid, melting point 85° to 86° C.

Workup

  1. temperaturewas warmed to 20° to 25° C.
  2. waitheld for one hour
  3. filtrationwater, filtered
  4. customdried
  5. customThe product was recrystallized from hexane

Sources & evidence

ORD record
ord-348426d9791541d2933d2c944324f8e0
Source dataset
uspto-grants-1983_05
Patent number
US04385104

Reaction notes

Loading…