3-Amino-4-methoxybenzoic acid → 3-[3-(2,4-Dichlorobenzoyl)ureido]-4-methoxybenzoic acid

HRID 1792744Notes

Reaction equation

HRID 1792744 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].[Cl:13][C:14]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:15]=1[C:16]([N:18]=[C:19]=[O:20])=[O:17]>C(#N)C>[Cl:13][C:14]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:15]=1[C:16]([NH:18][C:19](=[O:20])[NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6])=[O:17]

Participants

4

Reactant 2

HCID 178233-Amino-4-methoxybenzoic acidHCID 116298872,4-Dichlorobenzoyl isocyanate

Product 1

HCID 98862873-[3-(2,4-Dichlorobenzoyl)ureido]-4-methoxybenzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

20 g (120 mmol) of 3-amino-4-methoxybenzoic acid were made to react with 36 g (168 mmol) of 2,4-dichlorobenzoyl isocyanate from step a in 400 ml of acetonitrile and left to react therewith at reflux for 2 hours. After the mixture has cooled down to room temperature, the precipitate is filtered off with suction, washed twice with in each case 20 ml of acetonitrile, sucked dry and dried under high vacuum. 44 g (96%) of the desired product are obtained.

Workup

  1. waitleft
  2. customto react
  3. temperatureat reflux for 2 hours
  4. filtrationthe precipitate is filtered off with suction
  5. washwashed twice with in each case 20 ml of acetonitrile
  6. customsucked dry
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-a4215c2a13f74ffca2c62378fa5f5a43
Source dataset
uspto-grants-2006_07
Patent number
US07078404B2

Reaction notes

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