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

HRID 1276169Notes

Reaction equation

HRID 1276169 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-amino-4-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-5a3aee9e761a461f94463dbdad568a08
Source dataset
uspto-grants-2000_12
Patent number
US06166011

Reaction notes

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