Sulfuric Acid → HCID 67491343, compound

HRID 711047Notes

Reaction equation

HRID 711047 reaction equation
[I:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)(C)(C)C.C(OCC)(=O)C.O>[C:6]([N:4]1[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([I:1])=[N:3]1)([CH3:7])([CH3:2])[CH3:5]

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 178469927HCID 178469927, compound

Product 1

HCID 67491343HCID 67491343, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 3-iodo-1H-pyrazole-4-carboxylate (1.10 g, 3.91 mmol) in tert-butanol (5 mL) was added sulfuric acid (0.40 mL, 4.18 mmol, 18 M). The reaction was heated to 100° C. and stirred for 3 hours. The reaction was cooled to room temperature and diluted with ethyl acetate (100 mL) and water (25 mL). The pH was adjusted to 8 with saturated aqueous sodium bicarbonate. The layers were separated and the organics were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (7-60% ethyl acetate/heptanes) gave 2 regioisomeric products.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customThe layers were separated
  3. dry with materialthe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (7-60% ethyl acetate/heptanes)
  7. customgave 2 regioisomeric products

Sources & evidence

ORD record
ord-1cba429344b0486bbc95fb47bb7401f6
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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