Diisopropylethylamine → HCID 18412396, compound

HRID 50232

Reaction equation

HRID 50232 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:5]([C:7]1[CH:18]=[CH:17][C:10]2[N:11]([CH3:16])[C:12]([CH2:14]Cl)=[N:13][C:9]=2[CH:8]=1)=[O:6])[CH2:2][CH3:3].[C:26]([C:28]1[CH:33]=[CH:32][C:31]([SH:34])=[CH:30][CH:29]=1)#[N:27].C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH2:1]([N:4]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:5]([C:7]1[CH:18]=[CH:17][C:10]2[N:11]([CH3:16])[C:12]([CH2:14][S:34][C:31]3[CH:32]=[CH:33][C:28]([C:26]#[N:27])=[CH:29][CH:30]=3)=[N:13][C:9]=2[CH:8]=1)=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5850584-ThiobenzonitrileHCID 184123762-Chloromethyl-1-methylbenzimidazol-5-yl-carboxylic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide

Product 1

HCID 18412396HCID 18412396, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g (4.1 mmol) of 2-chloromethyl-1-methylbenzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide and 0.65 g (4.8 mmol) of p-cyanothiophenol was heated in 10 mL of dimethylformamide and 10 mL of diisopropylethylamine for 1 hour to 100° C. The solvent was distilled off in vacuo, the crude product was dissolved in 30 mL ethyl acetate, washed with 30 mL water, and after concentration purified by flash chromatography (silica gel; methylene chloride/ethanol (49:1 to 19:1). Yield: 1.5 g (79% of theory) of brown oil; Rf value: 0.65 (silica gel; ethyl acetate/ethanol/ammonia=90:10:1).

Workup

  1. distillationThe solvent was distilled off in vacuo
  2. dissolutionthe crude product was dissolved in 30 mL ethyl acetate
  3. washwashed with 30 mL water
  4. concentrationafter concentration
  5. custompurified by flash chromatography (silica gel

Sources & evidence

ORD record
ord-1ca23d3e2eb74acabf572c0c2a3704bf
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Linked notes

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