Chlorosuccinimide → HCID 68534690, compound

HRID 1192942Notes

Reaction equation

HRID 1192942 reaction equation
[Cl:1][CH:2]([C:13]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[F:20])[S:3]([C:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[O:8][N:7]=1)(=[O:5])=[O:4].[Cl:21]N1C(=O)CCC1=O>C1COCC1>[Cl:1][C:2]([Cl:21])([C:13]1[C:14]([F:20])=[CH:15][CH:16]=[CH:17][C:18]=1[F:19])[S:3]([C:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[O:8][N:7]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 59739546HCID 59739546, compound

Product 1

HCID 68534690HCID 68534690, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phosphazene base 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2 lambda5-5,4-lambda5-5-catenadi(phosphazene) (P2-tBu) (2M in THF) (0.38 ml, 0.77 mmol) was added dropwise at 0° C. to a solution of 3-[chloro-(2,6-difluoro-phenyl)methanesulfonyl]-5,5-dimethyl-4,5-dihydroisoxazole (prepared according to Example P3) (0.2 g, 0.64 mmol) in THF (5 ml). The solution was stirred for 10 minutes at room temperature. N-chlorosuccinimide (NCS) (0.10 g, 0.77 mmol) was added and the mixture was stirred for 1 hour at room temperature. The reaction was quenched by addition of aqueous hydrochloric acid (2M). The mixture was diluted with ethyl acetate and the two phases were separated. The organic phase was washed several times with brine, dried over magnesium sulfate and concentrated. The crude product was recrystallised from ethanol to give the product (Compound No. 1.26 of Table 27) as a white solid (110 mg, 48% yield).

Workup

  1. stirringthe mixture was stirred for 1 hour at room temperature
  2. customThe reaction was quenched by addition of aqueous hydrochloric acid (2M)
  3. additionThe mixture was diluted with ethyl acetate
  4. customthe two phases were separated
  5. washThe organic phase was washed several times with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe crude product was recrystallised from ethanol

Sources & evidence

ORD record
ord-33cc3f133a7a469dab0201ab746c19b1
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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