Hydrogen Bromide → N-[3-(Bromomethyl)phenyl]-N'-[4-(tetradecyloxy)phenyl]urea

HRID 653778Notes

Reaction equation

HRID 653778 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:15][CH:14]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[BrH:34]>C(O)(=O)C.C(Cl)(Cl)Cl>[Br:34][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:15][CH:14]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 10072687N-[3-(hydroxymethyl)phenyl]-N'-[4-(tetradecyloxy)phenyl]urea

Product 1

HCID 10481690N-[3-(Bromomethyl)phenyl]-N'-[4-(tetradecyloxy)phenyl]urea

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 10.0 g of N-[3-(hydroxymethyl)phenyl]-N'-[4-(tetradecyloxy)phenyl]urea, 70 ml of hydrogen bromide in acetic acid and 40 ml of chloroform is refluxed for 2.5 hours, then cooled. The solid is collected and washed with carbon tetrachloride and two times with water. The collected solid is crystallized from ethyl alcohol:tetrahydrofuran followed by recrystallization from tetrahydrofuran to give 7.4 g of the desired product as a white powder, m.p. 164°-169° C.

Workup

  1. temperatureis refluxed for 2.5 hours
  2. temperaturecooled
  3. customThe solid is collected
  4. washwashed with carbon tetrachloride and two times with water
  5. customThe collected solid is crystallized from ethyl alcohol
  6. customtetrahydrofuran followed by recrystallization from tetrahydrofuran

Sources & evidence

ORD record
ord-4aab1cfd7ea045c4aab772b335879cbc
Source dataset
uspto-grants-1992_07
Patent number
US05128351

Reaction notes

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