Hydrochloric Acid → HCID 19369069, compound

HRID 848950Notes

Reaction equation

HRID 848950 reaction equation
S(Cl)(Cl)(=O)=O.[CH:6]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:12]=[CH:11][C:10]=1[SH:18])([CH3:8])[CH3:7].[Cl:19][C:20]1[CH:25]=[C:24]([S:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=1[N:41]([C:45]1[CH2:49][C:48](=[O:50])[N:47]([C:51]2[C:56]([Cl:57])=[CH:55][C:54]([Cl:58])=[CH:53][C:52]=2[Cl:59])[N:46]=1)[C:42](=[O:44])[CH3:43].Cl>ClCCl.CN(C)C=O>[Cl:19][C:20]1[CH:25]=[C:24]([S:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])(=[O:27])=[O:28])[CH:23]=[CH:22][C:21]=1[N:41]([C:45]1[CH:49]([S:18][C:10]2[CH:11]=[CH:12][C:13]([CH:15]([CH3:17])[CH3:16])=[CH:14][C:9]=2[CH:6]([CH3:8])[CH3:7])[C:48](=[O:50])[N:47]([C:51]2[C:56]([Cl:57])=[CH:55][C:54]([Cl:58])=[CH:53][C:52]=2[Cl:59])[N:46]=1)[C:42](=[O:44])[CH3:43]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24648Sulfuryl chlorideHCID 15404891HCID 15404891, compoundHCID 19369060HCID 19369060, compound

Product 1

HCID 19369069HCID 19369069, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Sulfuryl chloride (6.2 g, 46 mmol) was added dropwise to a stirred solution of 2,4-diisopropylthiophenol (8.9 g, 46 mmol) in dichloromethane (50 ml) and stirring was continued at room temperature for 2 hrs. Volatiles were removed by rotary evaporation to give an oil. A solution of N-(2-chloro-4-dodecylsulfonylphenyl)-N-[4,5-dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]acetamide (29.0 g, 44 mmol) in N,N-dimethylformamide (75 ml) was added to the oil and the mixture was stirred at room temperature for 26 hrs. The solution was poured into 3N hydrochloric acid (750 ml) and the resulting sticky solid was collected by filtration. The solid was dissolved in ethyl acetate (200 ml) and the organic solution was washed with brine (100 ml), dried (MgSO4) and evaporated to an orange glass. The crude material was purified by column chromatography on 63-200 mesh silica gel eluting with 1:4 ethyl acetate/60-80 petroleum ether. Pure product was obtained as a cream colored glass, 11.7 g, 31%. C41H51Cl4N3O4S2Req: C 57.5%,H 6.0%,Cl 16.6%,N 4.9%,S 7.5%; Fd: C 57.1%,H 6.1%,Cl 16.4%,N 4.8%,S 7.2%

Workup

  1. customVolatiles were removed by rotary evaporation
  2. customto give an oil
  3. stirringthe mixture was stirred at room temperature for 26 hrs
  4. filtrationthe resulting sticky solid was collected by filtration
  5. dissolutionThe solid was dissolved in ethyl acetate (200 ml)
  6. washthe organic solution was washed with brine (100 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated to an orange glass
  9. customThe crude material was purified by column chromatography on 63-200 mesh silica gel eluting with 1:4 ethyl acetate/60-80 petroleum ether
  10. customPure product was obtained as a cream colored glass, 11.7 g, 31%

Sources & evidence

ORD record
ord-6210f9eefa4b41bd802442982d974955
Source dataset
uspto-grants-2000_01
Patent number
US06010837

Reaction notes

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