1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → methyl 4-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoate

HRID 2273592Notes

Reaction equation

HRID 2273592 reaction equation
CN(C)CCCN=C=NCC.[CH:12]([NH:15][C:16]1[C:17]([NH2:22])=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:14])[CH3:13].[N:23]([C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)=[C:24]=S>O1CCCC1.C(OCC)(=O)C>[CH:12]([N:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:22]=[C:24]1[NH:23][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1380024-Methoxycarbonylphenyl isothiocyanateHCID 105587871-N-(propan-2-yl)benzene-1,2-diamine

Product 1

HCID 67514178methyl 4-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoateYield 58.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide (EDC, 206 mg, 1.34 mmol) is added to a solution of N1-isopropylbenzene-1,2-diamine (100 mg, 0.67 mmol) and methyl 4-isothiocyanatobenzoate (138 mg, 0.67 mmol) in tetrahydrofuran. The reaction may be heated to reflux for a time period (for example 2 hours) and cooled to room temperature. The mixture may be diluted with ethyl acetate, filtered and concentrated. The residue may be purified by any method, including Biotage column chromatography to give methyl 4-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoate (122 mg)

Workup

  1. customThe reaction
  2. temperaturemay be heated
  3. customto reflux for a time period (for example 2 hours)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue may be purified by any method

Sources & evidence

ORD record
ord-fe6bba49e33c4255845a12e4fee52442
Source dataset
uspto-grants-2015_09
Patent number
US09125901B2

Reaction notes

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