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

HRID 2119397Notes

Reaction equation

HRID 2119397 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-ONEYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (13.6 g) was added to a solution of 2-amino4-iodophenylamine (13.2 g) [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-d81f0014085d457a99d34beda76967a7
Source dataset
uspto-grants-2004_02
Patent number
US06686357B1

Reaction notes

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