tert-Butyl cyanoacetate → HCID 69767014, compound

HRID 585770Notes

Reaction equation

HRID 585770 reaction equation
CN([CH:4]=[N:5][C:6]1[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]([N+:19]([O-:21])=[O:20])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])C.[C:22]([O:26][C:27](=[O:31])[CH2:28][C:29]#[N:30])([CH3:25])([CH3:24])[CH3:23]>C(O)(C)(C)C>[C:22]([O:26][C:27](=[O:31])[C:28]([C:29]#[N:30])=[CH:4][NH:5][C:6]1[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]([N+:19]([O-:21])=[O:20])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 70693tert-Butyl cyanoacetateHCID 86594636HCID 86594636, compound

Product 1

HCID 69767014HCID 69767014, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A 3-L round-bottomed flask under N2 equipped with an overhead stirrer, a condenser and a thermocouple is charged with 2-[[(dimethylamino)methylene]amino]-4-ethoxy-5-nitrobenzoic acid, methyl ester (68 g, 230 mmol), t-butanol (500 mL) followed by t-butylcyanoacetate (65 g, 460 mmol). The reaction mixture is heated to reflux. After 4 hours the reaction is cooled to room temperature and the suspension is filtered. The filter cake is washed with heptane (2×100 mL) and dried under vacuum (50 mm Hg) at 40° C. to provide the title compound as a beige solid (83 g, 91% yield, >98% purity by NMR). 1H NMR (300 MHz, DMSO-d6): 12.7 (d, J=12.9 Hz, 1H), 8.77 (d, J=12.9 Hz, 1H), 8.50 (s, 1H), 7.47 (s, 1H), 4.37 (q, J=7 Hz, 2H), 3.91 (s, 3H), 1.52 (s, 9H), 1.40 (t, J=7 Hz, 3H).

Workup

  1. customA 3-L round-bottomed flask under N2 equipped with an overhead stirrer, a condenser
  2. temperatureThe reaction mixture is heated to reflux
  3. filtrationthe suspension is filtered
  4. washThe filter cake is washed with heptane (2×100 mL)
  5. customdried under vacuum (50 mm Hg) at 40° C.

Sources & evidence

ORD record
ord-ea3868242e5245bba3ac6ef0c7a99377
Source dataset
uspto-grants-2005_08
Patent number
US06933388B2

Reaction notes

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