Toluene → 1-Hydroxy-4-(beta-methylsulfonylethoxy)-N-n-hexadecyl-2-naphthamide

HRID 126963Notes

Reaction equation

HRID 126963 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]=1[C:13]([NH:15][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][CH3:31])=[O:14].[CH3:32][S:33]([CH:36](O)[CH3:37])(=[O:35])=[O:34].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:37][CH2:36][S:33]([CH3:32])(=[O:35])=[O:34])=[CH:4][C:3]=1[C:13]([NH:15][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][CH3:31])=[O:14]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 30891342-Naphthalenecarboxamide, N-hexadecyl-1,4-dihydroxy-HCID 21979976Methanesulfonylethanol

Product 1

HCID 136436611-Hydroxy-4-(beta-methylsulfonylethoxy)-N-n-hexadecyl-2-naphthamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 g (0.023 mol) of 1,4-dihydroxy-N-n-hexadecyl-2-naphthamide, 5.7 g (0.046 mol) of methylsulfonylethanol and 4.4 g (0.023 mol) of p-toluenesulfonic acid were added to 50 ml of dehydrated toluene. The mixture was refluxed with heating for 5 hours and the water produced was removed. Toluene was removed under reduced pressure. 100 ml of methanol was added to the mixture. The crystals thus deposited were collected by filtration to obtain 10.8 g (88%) of Coupler (2). Melting Point: 107° to 109° C. (recrystallized from methanol).

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 5 hours
  3. customwas removed
  4. customToluene was removed under reduced pressure
  5. addition100 ml of methanol was added to the mixture
  6. filtrationThe crystals thus deposited were collected by filtration

Sources & evidence

ORD record
ord-0c77bb0b012e42618ef5473bf0aec8cb
Source dataset
uspto-grants-1981_03
Patent number
US04254212

Reaction notes

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