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Carbonate Ion → 2-{2-[(1,3-Dimethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-ylmethylene)-amino]-ethyl}-isoindole-1,3-dione

HRID 1828163
Notes
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Reaction equation

HRID 1828163 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[CH3:16][N:17]1[C:21]2[CH:22]=[CH:23][C:24]([CH:26]=O)=[CH:25][C:20]=2[N:19]([CH3:28])[C:18]1=[O:29].C(=O)([O-])[O-]>ClCCl>[CH3:16][N:17]1[C:21]2[CH:22]=[CH:23][C:24]([CH:26]=[N:2][CH2:3][CH2:4][N:5]3[C:6](=[O:15])[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:13]3=[O:14])=[CH:25][C:20]=2[N:19]([CH3:28])[C:18]1=[O:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 6054501,3-dimethyl-2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carbaldehydeHCID 220638492-(2-aminoethyl)-2,3-dihydro-1H-isoindole-1,3-dione hydrochloride

Product 1

HCID 220638072-{2-[(1,3-Dimethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-ylmethylene)-amino]-ethyl}-isoindole-1,3-dioneYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
22 °C

Procedure

To a dry flask charged with a stir bar was added 2-(2-amino-ethyl)-isoindole-1,3-dione hydrochloride salt (100 mg, 0.53 mmoles) (Burgess, K.; Ibarzo, J. D.; Linthicum S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; and Zhang, A.; J. Am. Chem. Soc. 1997, 119, 1556), 1,3-Dimethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbaldehyde (156 mg, 0.68 mmoles), MP-carbonate (254 mg, 0.79 mmoles) (Argonaut Tech), 3 Å sieves (1.2 g) and 4 mL of dichloromethane. The flask was sealed with a plastic cap and the resulting mixture was stirred for 48 hours at 22° C. The mixture was filtered through a nylon disk via syringes, rinsing with dichloromethane and the filtrate was concentrated to give 154 mg of 2-{2-[(1,3-Dimethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-ylmethylene)-amino]-ethyl}-isoindole-1,3-dione as a light yellow solid.

Workup

  1. additionTo a dry flask charged with a stir bar
  2. customThe flask was sealed with
  3. customa plastic cap
  4. filtrationThe mixture was filtered through a nylon disk via syringes
  5. washrinsing with dichloromethane
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8466c15215be4d788cc66ae3fa30d60f
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07056918B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes