1,1'-Carbonyldiimidazole → 5-IODO-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE

HRID 1635652Notes

Reaction equation

HRID 1635652 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:15]=1[NH2:21]>O1CCCC1>[I:20][C:18]1[CH:17]=[CH:16][C:15]2[NH:21][C:1](=[O:2])[NH:13][C:14]=2[CH:19]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 112070494-Iodobenzene-1,2-diamine

Product 1

HCID 120716615-IODO-1,3-DIHYDRO-BENZIMIDAZOL-2-ONE

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (13.6 g) was added to a solution of 2-amino-4-iodophenylamine (13.29) [see Makromol. Chem. (1993), 194(3), 859-868] in tetrahydrofuran (100 ml). The reaction mixture was stirred for 18 hours at room temperature, after which time the solvent was removed under reduced pressure, and the residue partitioned between 1N aqueous sodium hydroxide and diethyl ether. The aqueous was acidified with concentrated aqueous hydrochloric acid, and the resulting white precipitate filtered off and washed with water to afford 5-iodo-1,3-dihydro-2H-1,3-benzimidazol-2-one (14.0 g) as a white solid.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. customthe residue partitioned between 1N aqueous sodium hydroxide and diethyl ether
  3. filtrationthe resulting white precipitate filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-db854f2d6d574922b21a5b7f25fb69a7
Source dataset
uspto-grants-2003_01
Patent number
US06509464B1

Reaction notes

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