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

HRID 484599Notes

Reaction equation

HRID 484599 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-c03c3e7ef4ef4f8c914a68c4ab869820
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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