Chlorosuccinimide → HCID 90092618, compound

HRID 1774600Notes

Reaction equation

HRID 1774600 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)=[N:13][N:14]([CH3:18])[C:15]=3[CH:16]=[O:17])=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1.[Cl:24]N1C(=O)CCC1=O>C(#N)C>[Cl:24][C:21]1[S:20][C:19]([C:12]2[C:11]([C:9]3[CH:8]=[CH:7][C:6]4[O:1][CH2:2][CH2:3][CH2:4][C:5]=4[CH:10]=3)=[C:15]([CH:16]=[O:17])[N:14]([CH3:18])[N:13]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 90092444HCID 90092444, compound

Product 1

HCID 90092618HCID 90092618, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-3-(thiophen-2-yl)-1H-pyrazole-5-carbaldehyde (3d) (166 mg, 0.51 mmol) and N-chlorosuccinimide (67 mg, 0.50 mmol) in acetonitrile (18 mL) was heated overnight at 60° C. The reaction mixture was concentrated in vacuo. Water (10 mL) was added and the aqueous layer was extracted with ethyl acetate (2×12 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 80/20), to provide 3-(5-chlorothiophen-2-yl)-4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-1H-pyrazole-5-carbaldehyde (36a) (183 mg, 0.51 mmol, 99%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionWater (10 mL) was added
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×12 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-c08ffb262e7b443299e4e1e7010a22b8
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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