4-Chlorobutyrophenone → HCID 54553651, compound

HRID 613682Notes

Reaction equation

HRID 613682 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][CH2:20][NH:21][C:22](=[S:25])[NH:23][NH2:24]>C(O)C>[C:7]1([C:5](=[N:24][NH:23][C:22](=[S:25])[NH:21][CH2:20][CH2:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=2)[CH2:4][CH2:3][CH2:2][Cl:1])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 2535334-ChlorobutyrophenoneHCID 12722497N-[2-(2-Pyridinyl)ethyl]hydrazinecarbothioamide

Product 1

HCID 54553651HCID 54553651, compoundYield 117.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-chlorobutyrophenone (8.5 mL, 53 mmol) and 4-(2-(2-pyridyl)ethyl)-3-thiosemicarbazide (9.5 g, 48 mmol) in 400 mL of ethanol was heated under a nitrogen atmosphere to 75° C. and then at that temperature for 24 hours (overnight). The solvent was removed under reduced pressure to give 20.3 g of a yellow oil. This oil was triturated with EtOAc to separate the desired product from the thiosemicarbazide. The ethyl acetate was removed under reduced pressure and the residue chromatographed on 1 kg of silica gel (230-400 mesh) using 10-20% EtOAc-hexane as the eluent. The material collected (2.86 g, yellow solid) was recrystallized from isopropyl alcohol to give 2.30 g (13%) of the title compound as an off-white solid, mp 126-129° C.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6cc11419adb64e4f86698e4c02a08be9
Source dataset
uspto-grants-1999_12
Patent number
US06008362

Reaction notes

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