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

HRID 484592

Reaction equation

HRID 484592 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

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 962WaterSolventHCID 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-1d0883649c7d424994873662eac1dba4
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Linked notes

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