Chloroacetyl chloride → N'-(2-chloroacetyl)-N-(2-nitrophenyl)-N'-(3-bromo-4-ethoxyphenyl)-urea

HRID 2293908Notes

Reaction equation

HRID 2293908 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[C:16]([Br:23])[CH:15]=1)=[O:12])([O-:3])=[O:2].[Cl:24][CH2:25][C:26](Cl)=[O:27]>>[Cl:24][CH2:25][C:26]([N:13]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[C:16]([Br:23])[CH:15]=1)[C:11](=[O:12])[NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[O:27]

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 21473031N-(2-Nitrophenyl)-N'-(3-bromo-4-ethoxyphenyl)-urea

Product 1

HCID 21473025N'-(2-chloroacetyl)-N-(2-nitrophenyl)-N'-(3-bromo-4-ethoxyphenyl)-urea

Procedure

A solution containing N-(2-Nitrophenyl)-N'-(3-bromo-4-ethoxyphenyl)-urea (5.76 g) and chloroacetyl chloride (413 mL) was refluxed under nitrogen for 30 min. After the excess chloroacetyl chloride was removed in vacuo. diethyl ether (50 mL) was added and the resulting solid was filtered and dried to yield N'-(2-chloroacetyl)-N-(2-nitrophenyl)-N'-(3-bromo-4-ethoxyphenyl)-urea as a white solid.

Workup

  1. temperaturewas refluxed under nitrogen for 30 min
  2. customAfter the excess chloroacetyl chloride was removed in vacuo
  3. additiondiethyl ether (50 mL) was added
  4. filtrationthe resulting solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-92c9c31770fb4fa8a60905e19787b2b7
Source dataset
uspto-grants-1997_11
Patent number
US05688654

Reaction notes

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