Anisole → HCID 54400201, compound

HRID 263539Notes

Reaction equation

HRID 263539 reaction equation
C1(OC)C=CC=CC=1.COC1C=CC(C[O:16][N:17]([CH2:21][C:22]2[CH:58]=[CH:57][C:25]([C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34](=[O:56])[C:35]4[CH:40]=[CH:39][C:38]([CH2:41][N:42]([O:46]CC5C=CC(OC)=CC=5)[C:43]([NH2:45])=[O:44])=[CH:37][CH:36]=4)[CH:29]=3)=[O:27])=[CH:24][CH:23]=2)[C:18]([NH2:20])=[O:19])=CC=1>FC(F)(F)C(O)=O>[OH:46][N:42]([CH2:41][C:38]1[CH:39]=[CH:40][C:35]([C:34]([C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([C:26](=[O:27])[C:25]3[CH:57]=[CH:58][C:22]([CH2:21][N:17]([OH:16])[C:18]([NH2:20])=[O:19])=[CH:23][CH:24]=3)[CH:29]=2)=[O:56])=[CH:36][CH:37]=1)[C:43]([NH2:45])=[O:44]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 53637567HCID 53637567, compound

Product 1

HCID 54400201HCID 54400201, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

With ice-cooling, 10 ml of anisole and 40 ml of trifluoroacetic acid were added to 1.47 g of 1,3-bis[4-[[1-(4-methoxybenzyloxy)ureido]methyl]benzoyl]benzene. The reaction mixture was stirred with ice-cooling for 30 minutes and then at room temperature for 6 hours. The solvent was evaporated under a reduced pressure and the resulting residue was mixed with diethyl ether. The thus formed crystals were collected by filtration and dried to obtain 0.79 g of 1,3-bis[4-[(1-hydroxyureido)methyl]benzoyl]benzene.

Workup

  1. temperatureWith ice-cooling
  2. temperaturecooling for 30 minutes
  3. customThe solvent was evaporated under a reduced pressure
  4. additionthe resulting residue was mixed with diethyl ether
  5. filtrationThe thus formed crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-da8ce19a4e4a44c0833f5ecbd0f75be0
Source dataset
uspto-grants-1997_07
Patent number
US05643931

Reaction notes

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