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

HRID 235236Notes

Reaction equation

HRID 235236 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 (40 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, diethyl ether (50 mL)
  3. additionwas added
  4. filtrationthe resulting solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-70a122db8ab94ef0b90485c0866d1335
Source dataset
uspto-grants-1997_01
Patent number
US05597920

Reaction notes

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