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Pyridine → N-[3-(Hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamide

HRID 483560
Notes
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Reaction equation

HRID 483560 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].N1C=CC=CC=1.[CH2:16]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=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][CH3:29].C(Cl)(Cl)Cl>C(Cl)Cl.O>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([NH:1][C:35](=[O:36])[C:34]2[CH:33]=[CH:32][C:31]([O:30][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][CH3:29])=[CH:39][CH:38]=2)[CH:9]=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 802933-Aminobenzyl alcoholHCID 9998158Benzoyl chloride, 4-(tetradecyloxy)-

Product 1

HCID 10003333N-[3-(Hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 8.17 g of m-aminobenzyl alcohol and 16.14 g of pyridine in 200 ml of methylene chloride is added at 0° C. over 30 minutes a solution of 18 g of p-tetradecyloxybenzoyl chloride in 200 ml of methylene chloride. Stirring is continued for another 6 hours. An additional 400 ml of chloroform and water is added followed by warming to dissolve all the solids. The warm organic layer is separated and washed with dilute hydrochloric acid and saturated sodium bicarbonate. The warm organic layer is dried and filtered. The filtrate is diluted with an equal volume of hexane and cooled in a refrigerator overnight. The resulting solid is collected and air dried to give 18.4 g of the desired product as a white solid, m.p. 112°-115° C.

Workup

  1. temperatureby warming
  2. dissolutionto dissolve all the solids
  3. customThe warm organic layer is separated
  4. washwashed with dilute hydrochloric acid and saturated sodium bicarbonate
  5. customThe warm organic layer is dried
  6. filtrationfiltered
  7. additionThe filtrate is diluted with an equal volume of hexane
  8. temperaturecooled in a refrigerator overnight
  9. customThe resulting solid is collected
  10. customair dried

Sources & evidence

ORD record
ord-ee6686cdafc5499fad2c7154160a53da
Source dataset
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05225425

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes