Ethyl isocyanoacetate → HCID 14462625, compound

HRID 623726Notes

Reaction equation

HRID 623726 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](/[N+]([O-])=O)\[CH3:10])=[CH:4][CH:3]=1.[N+:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])#[C-:15]>CC(O)C.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH3:10])=[CH:15][NH:14][C:16]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 533707Ethyl isocyanoacetateHCID 1809354HCID 1809354, compound

Product 1

HCID 14462625HCID 14462625, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.6 mmol TBD/g polystyrene (21.4 g, 55.7 mmol) was added to a suspension of (E)-1-chloro-4-(2-nitroprop-1-enyl)benzene (10 g, 50.6 mmol) and ethyl 2-isocyanoacetate (6.01 g, 53.1 mmol) in i-PrOH (40 mL) and dry THF (40 mL). The reaction mixture was stirred at room temperature overnight. The suspension was filtered, washed with i-PrOH/THF (1/1, v/v, 40 mL). The combined filtrate was evaporated under reduced pressure to furnish 11.0 g (82%) of the desired product.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with i-PrOH/THF (1/1, v/v, 40 mL)
  3. customThe combined filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-89f852d7363f4567a0a3d4d47fd8ce51
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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