Ethyl acetamidocyanoacetate → Ethyl 2-cyano-2-acetamido-2-(2,3-dihydro-1H-inden-2yl)acetate

HRID 615695Notes

Reaction equation

HRID 615695 reaction equation
[O-]CC.[Na+].[C:5]([NH:8][CH:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6].Br[CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1>CS(C)=O>[C:15]([C:9]([NH:8][C:5](=[O:7])[CH3:6])([CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:16]

Participants

5

Reactant 3

HCID 95422Ethyl acetamidocyanoacetateHCID 2723922Sodium ethoxideHCID 109654632-bromo-2,3-dihydro-1H-indene

Product 1

HCID 13517005Ethyl 2-cyano-2-acetamido-2-(2,3-dihydro-1H-inden-2yl)acetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Sodium ethoxide (40 gms) was stirred in 1 L of dimethyl sulfoxide until solution was complete. Then, 100 g of ethyl acetamido-cyanoacetate was added, and again stirred until solution was complete. 2-Bromoindane (101 g) was slowly added, using a few ml of DMSO to wash the container and addition funnel. The solution was stirred over a weekend.

Workup

  1. washto wash
  2. additionthe container and addition funnel
  3. stirringThe solution was stirred over a weekend

Sources & evidence

ORD record
ord-9fb38fe8ea064d439ab89cb9e2234f71
Source dataset
uspto-grants-1985_02
Patent number
US04500713

Reaction notes

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