1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 9797986, compound

HRID 613443Notes

Reaction equation

HRID 613443 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([CH3:17])([CH3:16])[CH:10](OC(=O)C)[CH:9]2[N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[CH2:2][CH2:3][CH3:4].C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CC(=O)OCC>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([CH3:16])([CH3:17])[CH:10]=[C:9]2[N:22]([CH3:27])[S:23]([CH3:26])(=[O:24])=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19593314HCID 19593314, compound

Product 1

HCID 9797986HCID 9797986, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.5 g (1.3 mmol) of N-(6-butoxy-3-acetoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide (Example 6) and 1.1 g (7.5 mmol) of DBU in 2.5 ml of toluene was heated at 105° C. for 60 h. The reaction mixture was diluted with EA and washed with hydrochloric acid until the aqueous phase gave an acidic reaction. The mixture was washed with sodium bicarbonate solution, dried over magnesium sulfate and concentrated i. vac., giving 0.3 9 of N-(6-butoxy-2,2-dimethyl-2H-chromen-4-yl)-N-methyl-methanesulfonamide; m.p. 114-116° C.

Workup

  1. washwashed with hydrochloric acid until the aqueous phase
  2. customgave
  3. customan acidic reaction
  4. washThe mixture was washed with sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated i

Sources & evidence

ORD record
ord-12ad30c2c22d49fbbb031808bd78578b
Source dataset
uspto-grants-1999_12
Patent number
US06008245

Reaction notes

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