Diisopropylcarbodiimide → 2-[(4-acetylphenyl)amino]-1-[2-(1,3-dioxolan-2-yl)ethyl]-N,N-bis(3-methylbutyl)-1H-benzimidazole-6-carboxamide

HRID 1784306Notes

Reaction equation

HRID 1784306 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=S)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(N=C=NC(C)C)(C)C.[NH2:22][C:23]1[CH:41]=[CH:40][C:26]([C:27]([N:29]([CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:28])=[CH:25][C:24]=1[NH:42][CH2:43][CH2:44][CH:45]1[O:49][CH2:48][CH2:47][O:46]1>O1CCCC1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:42]([CH2:43][CH2:44][CH:45]3[O:46][CH2:47][CH2:48][O:49]3)[C:24]3[CH:25]=[C:26]([C:27]([N:29]([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:35][CH2:36][CH:37]([CH3:38])[CH3:39])=[O:28])[CH:40]=[CH:41][C:23]=3[N:22]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 2427791-(4-Isothiocyanatophenyl)ethanoneHCID 68792502HCID 68792502, compound

Product 1

HCID 687918172-[(4-acetylphenyl)amino]-1-[2-(1,3-dioxolan-2-yl)ethyl]-N,N-bis(3-methylbutyl)-1H-benzimidazole-6-carboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-acetylphenyl isothiocyanate (1.1 g, 1.2 eq) and diisopropylcarbodiimide (1.95 g, 3 eq) are successively added to a solution of 4-amino-3-{[2-(1,3-dioxolan-2-yl)ethyl]amino}-N,N-bis(3-methylbutyl)benzamide (2 g, 1 eq) in tetrahydrofuran (50 ml). The mixture is heated under reflux for 18 hours then cooled down to ambient temperature and concentrated under reduced pressure at 40° C. Water (100 ml) and dichloromethane (200 ml) are added to the residue obtained. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent:heptane/ethyl acetate 4:6) produces the expected compound in the form of a white foam (1.8 g; 66% yield).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. concentrationconcentrated under reduced pressure at 40° C
  4. additionWater (100 ml) and dichloromethane (200 ml) are added to the residue
  5. customobtained
  6. extractionAfter decantation and extractions
  7. washthe combined organic phases are washed with salt water
  8. dry with materialdried over Na2SO4
  9. concentrationthen concentrated under reduced pressure at 40° C
  10. customPurification of the residue by flash chromatography on silica gel (eluent:heptane/ethyl acetate 4:6)

Sources & evidence

ORD record
ord-5d98e5e0bf7c435689749e9524e0a37d
Source dataset
uspto-grants-2009_03
Patent number
US07501525B2

Reaction notes

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