Tert-butyldicarbonate → HCID 22929887, compound

HRID 1295924Notes

Reaction equation

HRID 1295924 reaction equation
[CH3:1][NH:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[C:7]([CH3:12])=[CH:6][C:5]=1[O:13][CH2:14][CH3:15].[C:17]([O:24]C([O-])=O)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O>C(#N)C.CN(C1C=CC=CN=1)C>[C:10]([C:8]1[C:7]([CH3:12])=[CH:6][C:5]([O:13][CH2:14][CH3:15])=[C:4]([CH:9]=1)[C:3]([N:2]([CH3:1])[C:17](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:16])#[N:11]

Participants

5

Reactant 2

HCID 22064466Tert-butyldicarbonate2×HCID 229298705-Cyano-2-ethoxy-N,4-dimethylbenzamide

Product 1

HCID 22929887HCID 22929887, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

After suspending N1,4-dimethyl-5-cyano-2-ethoxybenzamide (92 g) in acetonitrile (11), tert-butyl dicarbonate (110 g) and dimethylaminopyridine (2.6 g) were added and the mixture was stirred at room temperature overnight. The reaction mixture was heated to 90° C. and stirred for 3 hours. tert-Butyl dicarbonate (110 g) was further added and the mixture was stirred at 50° C. overnight. After cooling to room temperature, the precipitated crystals were filtered off (24.3 g). The filtrate was concentrated and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (81.1 g) as a white solid.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was heated to 90° C.
  3. stirringstirred for 3 hours
  4. stirringthe mixture was stirred at 50° C. overnight
  5. temperatureAfter cooling to room temperature
  6. filtrationthe precipitated crystals were filtered off (24.3 g)
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-15dbb5cd070d4e1db8afd5dbbdfae712
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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