Sodium hydride → HCID 86758357, compound

HRID 2229429Notes

Reaction equation

HRID 2229429 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:8][N:9]1[C:13]2[C:14]([CH2:18]C(OCC)=O)=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]1=[O:24].BrC[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>CC(N(C)C)=O>[CH3:31][O:30][C:26]1[CH:25]=[C:7]([CH:6]=[C:5]([O:4][CH3:3])[C:27]=1[O:28][CH3:29])[CH2:8][N:9]1[C:13]2[C:14]([CH2:18][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]1=[O:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68320Ethyl 3-bromopropionateHCID 70179203HCID 70179203, compound

Product 1

HCID 86758357HCID 86758357, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Procedure

Sodium hydride (14.1 mmol, 0.56 g, 60% mineral oil) is dissolved in dimethylacetamide (10 ml). 1-(3,4,5-trimethoxybenzyl)-3-hydrobenzimidazol-2-one (9.1 mmol, 2.86 g) (example 10) in dimethylacetamide (10 ml) is added dropwise to the ice cooled solution which is stirred for 1 hour. Ethyl 3-bromopropionate (14.1 mmol, 1.79 ml, 2.53 g) in dimethyl-acetamide (5 ml) is added, and the mixture is stirred 24 hours at room temperature. The solution is added dropwise into ice (300 g), and the precipitate is filtered off, added to a 1:1 dichloromethane/water mixture and is extracted with dichloromethane (3×20 ml). The combined organic layers are dried with MgSO4, filtered and evaporated. Recrystallisation from ethyl acetate (5 ml) yields the title compound (R1=(CH2)2—C(O)—OEt, R2=3,4,5-trimethoxybenzyl, x=2, n=0).

Workup

  1. stirringthe mixture is stirred 24 hours at room temperature
  2. filtrationthe precipitate is filtered off
  3. additionadded to a 1:1 dichloromethane/water mixture
  4. extractionis extracted with dichloromethane (3×20 ml)
  5. dry with materialThe combined organic layers are dried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customRecrystallisation from ethyl acetate (5 ml)

Sources & evidence

ORD record
ord-5bcc7a8a78554561b125bbf65ebedf33
Source dataset
uspto-grants-2002_07
Patent number
US06420410B1

Reaction notes

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