3-Chloro-1,2-benzisothiazole → HCID 136365467, compound

HRID 418454Notes

Reaction equation

HRID 418454 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:13])[C:5]([CH3:12])=[C:6]2[C:10]=1[NH:9][C:8]([CH3:11])=[CH:7]2.Cl[C:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[S:17][N:16]=1>CN1C(=O)CCC1.Cl.O1CCOCC1>[S:17]1[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:15]([C:7]2[C:6]3[C:10](=[C:2]([Cl:1])[CH:3]=[C:4]([F:13])[C:5]=3[CH3:12])[NH:9][C:8]=2[CH3:11])=[N:16]1

Participants

6

Reactant 2

HCID 5981903-Chloro-1,2-benzisothiazoleHCID 21077850HCID 21077850, compound

Product 1

HCID 136365467HCID 136365467, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of the product from step b) (200 mg) and 3-chloro-1,2-benzisothiazole (171 mg) in NMP (2 ml) and 4M hydrogen chloride in dioxan (0.2 ml) was stirred at 140° C. overnight and then at 150° C. for 1 hour, and evaporated. The residue was taken up in ethyl acetate, washed with brine (3×), dried (MgSO4) and evaporated. The residue was purified by silica chromatography using 20% acetone in isohexane as eluent to give the title compound (219 mg).

Workup

  1. customevaporated
  2. washwashed with brine (3×)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-affc8d4b3b334a289bfd2c6724800c2a
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

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