Chloroacetonitrile → HCID 21223924, compound

HRID 1584126Notes

Reaction equation

HRID 1584126 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[H-].[Na+].Cl[CH2:19][C:20]#[N:21]>CN(C=O)C>[C:20]([CH2:19][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:21]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 259091Ethyl 5-Bromoindole-2-carboxylate

Product 1

HCID 21223924HCID 21223924, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-2 (11.2 g, 44.4 mmol) in DMF (400 mL) was treated with NaH (3.2 g of 60% dispersion in oil, 66.6 mmol) for 0.5 hour and then chloroacetonitrile (Aldrich, 5.6 mL, 88.8 mmol) was added and the reaction was stirred overnight. The solvent was removed in vacuo and the residue was partitioned between water and EtOAc. The water layer was extracted with EtOAc, the organic layers were combined, washed with water, brine, dried with MgSO4, filtered and evaporated to give 2-3 as a brown solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and EtOAc
  3. extractionThe water layer was extracted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-668a76fef7c54f5f82c05dfca80df30e
Source dataset
uspto-grants-1999_08
Patent number
US05932582

Reaction notes

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