Water → HCID 70792370, compound

HRID 2405030Notes

Reaction equation

HRID 2405030 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH:15][CH2:16][CH2:17][C:18]#[N:19])=[N:12][O:13][N:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26]([O:33][C:34](=[O:46])[NH:35][C:36]1[CH:41]=[CH:40][C:39]([C:42](=[O:45])[CH2:43]Br)=[CH:38][CH:37]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C)C=O.C(OCC)(=O)C.CO>[CH2:26]([O:33][C:34](=[O:46])[NH:35][C:36]1[CH:37]=[CH:38][C:39]([C:42](=[O:45])[CH2:43][N:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=[C:2]2[C:10]2[C:11]([NH:15][CH2:16][CH2:17][C:18]#[N:19])=[N:12][O:13][N:14]=2)=[CH:40][CH:41]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18981260Benzyl [4-(bromoacetyl)phenyl]carbamateHCID 1363893133-[4-(1H-Benzoimidazol-2-yl)-furazan-3-ylamino]-propionitrile

Product 1

HCID 70792370HCID 70792370, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To a stirred solution of 11.1 g of 3-[4-(1H-benzoimidazol-2-yl)-furazan-3-ylamino]-propionitrile (95%, 41.5 mmol, 1 eq) in 90 ml of N,N-dimethylformamide are added 7.84 g of potassium carbonate (56.8 mmol, 1.3 eq), followed by 23.25 g of [4-(2-bromo-acetyl)-phenyl]-carbamic acid benzyl ester (75%, 50.1 mmol, 1.2 eq). The reaction mixture is stirred for 4 h at room temperature. Then 700 ml of water are added and the resulting suspension is extracted with 3×800 ml of ethyl acetate. The combined organic layers are washed with water and brine, dried over Na2SO4, filtered and concentrated to give the crude product as dark brown solid. This crude product is suspended in 150 ml of a 2/1 ethyl acetate/methanol mixture. Filtration provides 12.63 g of the desired product as light brown powder.

Workup

  1. extractionthe resulting suspension is extracted with 3×800 ml of ethyl acetate
  2. washThe combined organic layers are washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product as dark brown solid
  7. filtrationFiltration

Sources & evidence

ORD record
ord-e716279eee944260b808de85f52190a8
Source dataset
uspto-grants-2014_08
Patent number
US08802858B2

Reaction notes

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