Sodium Hydroxide → Apararenone

HRID 1479788Notes

Reaction equation

HRID 1479788 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3[CH:14]=[CH:15][C:16]([N:18](S(C)(=O)=O)[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][C:12]=3[O:11][C:10]([CH3:28])([CH3:27])[C:9]2=[O:29])=[CH:4][CH:3]=1.[OH-].[Na+].CC1(C)C(=O)NC2C=CC(N(S(C)(=O)=O)S(C)(=O)=O)=CC=2O1.Cl.C(O)C.O>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13]3[CH:14]=[CH:15][C:16]([NH:18][S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][C:12]=3[O:11][C:10]([CH3:27])([CH3:28])[C:9]2=[O:29])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 73294711N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-N-(methylsulfonyl)methanesulfonamideHCID 73297136N-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-N-(methylsulfonyl)methanesulfonamideHCID 86604601Ethanol water hydrochloric acid

Product 1

HCID 24744336ApararenoneYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-N-(methylsulfonyl)methanesulfonamide (1 g) in ethanol (3 mL) was added dropwise an aqueous sodium hydroxide solution (0.18 g/3 mL) at 25° C., then ethanol/water (1:1.2 mL) was added thereto, and the mixture was stirred overnight at the same temperature. To the reaction mixture was added dropwise concentrated hydrochloric acid/ethanol/water (0.24 g/0.5 mL/0.35 mL) at 25° C., and the mixture was stirred for 1 hour. The precipitated crystals were collected by filtration, washed with a solution of ethanol/water (1:1.6 mL), and then dried under reduced pressure at 50° C. to obtain the title compound (0.80 g) as Form B crystals (yield: 98%, purity: 95%).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with a solution of ethanol/water (1:1.6 mL)
  4. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-1f2c8fd913b4467ab88a08786b9a42a2
Source dataset
uspto-grants-2016_08
Patent number
US09409874B2

Reaction notes

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