1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67514421, compound

HRID 2273603Notes

Reaction equation

HRID 2273603 reaction equation
CN(C)CCCN=C=NCC.[CH3:12][O:13][CH2:14][CH2:15][NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][C:18]=1[N+:29]([O-])=O.[N:32]([C:35]1[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=1)=[C:33]=S>O1CCCC1.C(OCC)(=O)C>[CH3:12][O:13][CH2:14][CH2:15][N:16]1[C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][C:18]=2[N:29]=[C:33]1[NH:32][C:35]1[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1380024-Methoxycarbonylphenyl isothiocyanateHCID 67506721HCID 67506721, compound

Product 1

HCID 67514421HCID 67514421, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide (EDC, 200 mg, 1.44 mg) is added to a solution of N-(2-methoxyethyl)-3-nitrobiphenyl-4-amine (119 mg, 0.48 mmol) and methyl 4-isothiocyanatobenzoate (83 mg, 0.43 mmol) in tetrahydrofuran. The reaction may reflux for an appropriate time period, such as 2 hours and cooled. The mixture may be diluted with ethyl acetate, filtered and concentrated. The residue may be purified by any appropriate method including Biotage column chromatography to give methyl 4-(1-(2-methoxyethyl)-5-phenyl-1H-benzo[d]imidazol-2-ylamino)benzoate (96 mg)

Workup

  1. customThe reaction
  2. temperaturemay reflux for an appropriate time period, such as 2 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue may be purified by any appropriate method

Sources & evidence

ORD record
ord-6f89ce22baef41dba3c76cc99df9f250
Source dataset
uspto-grants-2015_09
Patent number
US09125901B2

Reaction notes

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