Pyridine → HCID 23456162, compound

HRID 1680394Notes

Reaction equation

HRID 1680394 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([S:10](Cl)(=[O:12])=[O:11])=[CH:4][N:3]=1.[NH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([OH:25])=[C:17]([C:26]([N:28]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[O:27])[CH:16]=1.N1C=CC=CC=1>N1C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([S:10]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([OH:25])=[C:17]([C:26]([N:28]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[O:27])[CH:16]=2)(=[O:12])=[O:11])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1033282-Naphthalenecarboxamide, 4-amino-1-hydroxy-N,N-dioctadecyl-HCID 23456146HCID 23456146, compound

Product 1

HCID 23456162HCID 23456162, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

A mixture of 2-chloro-5-chlorosulfonyl-3-methoxypyridine (0.65 g, 2.68×10-3 mole) (see Example 9), 4-amino-N,N-dioctadecyl-1-hydroxy-2-naphthamide (1.40 g, 1.98×10-3 mole) and pyridine (0.20 g, 2.5×10-3 mole) was stirred overnight at room temperature. Additional pyridine (7 drops) was employed after the first 21/2 hours of stirring. The reaction mixture was concentrated in vacuo and diluted with water to precipitate an oil which changed to a waxy solid upon trituration with water. The waxy solid was dissolved in toluene and purified by column chromatography on silica gel using toluene. The toluene fraction was concentrated to a solid which was recrystallized from ethanol; yield, 0.40 g (22 percent), m.p. 85° to 87° C.

Workup

  1. custom2 hours
  2. stirringof stirring
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with water
  5. customto precipitate an oil which
  6. dissolutionThe waxy solid was dissolved in toluene
  7. custompurified by column chromatography on silica gel
  8. concentrationThe toluene fraction was concentrated to a solid which
  9. customwas recrystallized from ethanol
  10. customyield

Sources & evidence

ORD record
ord-c4f71dda342349beb8c18a1541c33388
Source dataset
uspto-grants-1981_06
Patent number
US04273706

Reaction notes

Loading…