Water → N-[3-(hydroxymethyl)phenyl]-N'-[4-(tetradecyloxy)phenyl]urea

HRID 2227057Notes

Reaction equation

HRID 2227057 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[NH2:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][OH:30].O>O1CCCC1.N1C=CC=CC=1>[OH:30][CH2:29][C:28]1[CH:27]=[C:26]([NH:25][C:23]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:21][CH:20]=2)=[O:24])[CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 962WaterHCID 802933-Aminobenzyl alcoholHCID 11724283p-(Tetradecyloxy)phenyl isocyanate

Product 1

HCID 10072687N-[3-(hydroxymethyl)phenyl]-N'-[4-(tetradecyloxy)phenyl]ureaYield 73.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of 13 g of p-(tetradecyloxy)phenyl isocyanate in 70 ml of tetrahydrofuran and 30 ml of pyridine is added over 10 minutes a solution of 7.24 g of 3-aminobenzyl alcohol in 70 ml of tetrahydrofuran with continued stirring for one hour. The mixture is heated until all the solids dissolve then allowed to stand at ambient temperature overnight. The mixture is poured into water and the solid collected. The solid is washed with dilute hydrochloric acid and water then crystallized from ethyl alcohol to give 13.1 g of the desired product as a light pink solid, m.p. 150°-158° C.

Workup

  1. temperatureThe mixture is heated until all the solids
  2. dissolutiondissolve
  3. waitto stand at ambient temperature overnight
  4. customthe solid collected
  5. washThe solid is washed with dilute hydrochloric acid and water
  6. customthen crystallized from ethyl alcohol

Sources & evidence

ORD record
ord-609be492718f44b9aa0ba48946a08bd8
Source dataset
uspto-grants-1994_09
Patent number
US05350759

Reaction notes

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