N-bromobutanimide → HCID 90092720, compound

HRID 1774562Notes

Reaction equation

HRID 1774562 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[CH:5][C:4]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)=[N:3]1.[Br:14]N1C(=O)CCC1=O>C(#N)C.[O-2].[O-2].[Mn+4]>[Br:14][C:5]1[C:4]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)=[N:3][N:2]([CH3:1])[C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 90095142HCID 90095142, compound

Product 1

HCID 90092720HCID 90092720, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of [1-methyl-3-(thiophen-3-yl)-1H-pyrazol-5-yl]methanol (4b) (271 mg, 1.39 mmol) and N-bromosuccinimide (236 mg, 1.32 mmol) in acetonitrile (23 mL) was stirred at room temperature for 1 hour. 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 taken in dichloromethane (5 mL) and manganese dioxide (1.21 g, 13.95 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours, filtered over Celite®, and the filtrate was concentrated in vacuo. to provide 4-bromo-1-methyl-3-(thiophen-3-yl)-1H-pyrazole-5-carbaldehyde (4c) (297 mg, 1.10 mmol, 78%), which was used without further purification.

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. filtrationfiltered over Celite®
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7cc25872d2fb46d0a51db738dfc64eab
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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