Diphosgene → HCID 59864978, compound

HRID 1958565Notes

Reaction equation

HRID 1958565 reaction equation
[CH2:1]([C:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]([CH3:17])([CH3:16])[NH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].CCN(C(C)C)C(C)C.[Cl:27][C:28](OC(Cl)(Cl)Cl)=[O:29]>ClCCl>[CH2:1]([C:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]([CH3:16])([CH3:17])[N:7]([C:28]([Cl:27])=[O:29])[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10426DiphosgeneHCID 81531DiisopropylethylamineHCID 598649343-(n-Butyl)-5,5-dimethyl-4-phenyl-4,5-dihydropyrazole

Product 1

HCID 59864978HCID 59864978, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 3-(n-butyl)-5,5-dimethyl-4-phenyl-4,5-dihydropyrazole (Intermediate (IV-1) (0.47 gram, 1.43 mmol) in dichloromethane (10 ml) was successively added DIPEA (0.35 ml, 2.07 mmol) and trichloromethyl chloroformate (0.25 ml, 2.07 mmol, dissolved in 10 ml dichloromethane) at 0° C. and the resulting solution was allowed to attain room temperature and subsequently reacted at room temperature for 1 hour in a nitrogen atmosphere. Subsequent Sepacore column chromatographic purification (eluant: petroleum ether/diethyl ether=93/7 (v/v)) gave pure 3-(n-butyl)-5,5-dimethyl-4-phenyl-4,5-dihydro-(1H)-pyrazole-1-carbonyl chloride (Intermediate VIII-1) (0.20 g, 43% yield). (Intermediate VIII-1). 1H-NMR (400 MHz, CDCl3) δ 0.87 (t, J=7, 3H), 1.11 (s, 3H), 1.27-1.39 (m, 2H), 1.45-1.59 (m, 5H), 2.10-2.20 (m, 1H), 2.36-2.46 (m, 1H), 3.91 (s, 1H), 7.01 (br d, J˜8 Hz, 2H), 7.30-7.40 (m, 3H).

Workup

  1. customat 0° C.
  2. customto attain room temperature
  3. customsubsequently reacted at room temperature for 1 hour in a nitrogen atmosphere
  4. customSubsequent Sepacore column chromatographic purification (eluant: petroleum ether/diethyl ether=93/7 (v/v))

Sources & evidence

ORD record
ord-910d60252cc5448e9331f681da1dd1c5
Source dataset
uspto-grants-2013_04
Patent number
US08410135B2

Reaction notes

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