4-Methylmorpholine → 4-(Pyridin-2-yl)-benzoic acid iso-butyloxyformic acid anhydride

HRID 380232Notes

Reaction equation

HRID 380232 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.CN1CCOCC1.Cl[C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25]>C1COCC1>[CH2:27]([O:26][C:24]([O:12][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:8][CH:9]=1)=[O:25])[CH:28]([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 8216924-(2-Pyridyl)Benzoic Acid

Product 1

HCID 543403644-(Pyridin-2-yl)-benzoic acid iso-butyloxyformic acid anhydride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

With the exclusion of air, 6.0 g (30 mmol) of 4-(pyridin-2-yl)-benzoic acid are suspended at −20° C. in 90 ml of THF, and 9.90 ml (90 mmol) of N-methyl-morpholine and 4.32 ml (33 mmol) of isobutyl chloroformate are added. After 30 min, the mixture is filtered, washed with a small amount of cold THF, and the filtrate is partially concentrated by evaporation; the residue is diluted with methylene chloride, washed with ice-water and cold brine, dried (Na2SO4) and concentrated by evaporation to form the title compound: 1H-NMR (CDCl3) i.a. 8.75 (m, 1H), 8.16 (AB, J=8, 4H), 7.81 (m, 2H), 7.32 (4-line system, J=5, 1H), 4.16 (d, J=7, 2H), 2.10 (9-line system, J=7, 1H), 1.02 (d, J=7, 6H).

Workup

  1. filtrationthe mixture is filtered
  2. washwashed with a small amount of cold THF
  3. concentrationthe filtrate is partially concentrated by evaporation
  4. additionthe residue is diluted with methylene chloride
  5. washwashed with ice-water and cold brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-60ce3e9fef9549d48ede5f3d69b1880b
Source dataset
uspto-grants-2001_10
Patent number
US06300519B1

Reaction notes

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