1-Butanol → 3-(Butylamino)-5-(4-chlorophenyl)-1H-pyrazole-4-acetic acid butyl ester

HRID 345507Notes

Reaction equation

HRID 345507 reaction equation
[CH2:1]([NH:5][C:6](=S)[NH:7][NH2:8])[CH2:2][CH2:3][CH3:4].Cl.[Cl:11][C:12]1[CH:26]=[CH:25][C:15]([C:16]([CH:18](Cl)[CH2:19][C:20]([O:22][CH3:23])=[O:21])=O)=[CH:14][CH:13]=1.[CH2:27](O)[CH2:28][CH2:29]C>O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][C:18]1[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[N:7][NH:8][C:16]=1[C:15]1[CH:25]=[CH:26][C:12]([Cl:11])=[CH:13][CH:14]=1)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 18103033-Amino-1-butylthioureaHCID 19992468HCID 19992468, compound

Product 1

HCID 538648703-(Butylamino)-5-(4-chlorophenyl)-1H-pyrazole-4-acetic acid butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.9 g (0.04 mole) of 4-butyl-3-thiosemicarbazide, 3.3 ml (0.04 mole) of 37% hydrochloric acid and 10.5 g (0.04 mole) of methyl 3-(4-chlorobenzoyl)-3-chloropropionate in 150 ml of 1-butanol was stirred at ambient temperature for 4 hours and heated at reflux for 40 hours. The reaction mixture was diluted with 50 ml of water, filtered to remove the inorganic sulfur, then concentrated in vacuo (19 g). The residue was placed on a 400 g Florisil column and eluted with benzene then with an acetone:benzene gradient (0.5 to 10%). The product fractions were combined and concentrated in vacuo to give 15.2 g of pale yellow solid. Recrystallization from 2-propanol yielded 2 g (14%) of fluffy white crystals, mp 130°-130.5° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 40 hours
  3. filtrationfiltered
  4. customto remove the inorganic sulfur
  5. concentrationconcentrated in vacuo (19 g)
  6. washeluted with benzene
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75e8b4f2b7ba4417b0102417428b761c
Source dataset
uspto-grants-1991_10
Patent number
US05057534

Reaction notes

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