Sodium Carbonate → HCID 25052269, compound

HRID 1818030Notes

Reaction equation

HRID 1818030 reaction equation
S1CCCS[CH:2]1[C:7]1[CH2:12][CH2:11][CH2:10][CH:9]([NH:13][C:14]([NH:16][CH2:17][CH2:18][F:19])=[O:15])[C:8]=1[CH3:20].ClN1C(=[O:27])CCC1=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>CC#N.O.[N+]([O-])([O-])=O.[Ag+]>[F:19][CH2:18][CH2:17][NH:16][C:14]([NH:13][CH:9]1[CH2:10][CH2:11][CH2:12][C:7]([CH:2]=[O:27])=[C:8]1[CH3:20])=[O:15]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 57884208HCID 57884208, compound

Product 1

HCID 25052269HCID 25052269, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

1-(3-[1,3]Dithian-2-yl-2-methyl-cyclohex-2-enyl)-3-(2-fluoro-ethyl)-urea (630 mg, 2.00 mmol) dissolved in 3 mL CH3CN was added to a solution of N-chlorosuccinimide (845 mg, 6.30 mmol) and AgNO3 (1.24 g, 7.30 mmol) in 14 mL of 80% aqueous CH3CN at 0° C. The reaction mixture was stirred for 30 minutes, and then 3.60 g of Na2S2O3 in 7.0 mL of H2O was added, followed by 4.20 g of Na2CO3 in 7.0 mL of H2O. The resulting mixture was stirred for 5 minutes and filtered through a pad of celite. The celite was washed with EtOAc and the combined organic phases were washed with brine (1×15 mL), dried over MgSO4 and concentrated. Purification by column chromatography using hexane:EtOAc (4:1) as the eluant gave the desired title urea. Spectroscopic data: 1H NMR (500 MHz, DMSO-d6) δ 1.49-1.58 (m, 3H), 1.60-1.67 (m, 1H), 1.92-2.00 (m, 1H), 2.08-2.14 (m, 4H), 3.29 (q, J=4.88 Hz, 1H), 3.35 (q, J=5.86, 4.88 Hz, 1H), 4.20-4.25 (m, 1H), 4.35 (t, J=4.88 Hz, 1H), 4.45 (t, J=4.88 Hz, 1H), 6.01 (t, J=5.37 Hz, 1H), 6.28 (d, J=8.79 Hz, 1H), 10.1 (s, 1 H). 13C NMR (126 MHz, DMSO-d6) δ 15.62, 18.72, 22.79, 30.23, 40.62 (d, J=20.14 Hz), 50.08, 84.04 (d, J=163.98 Hz), 134.63, 155.68, 158.31, 193.00.

Workup

  1. stirringThe resulting mixture was stirred for 5 minutes
  2. filtrationfiltered through a pad of celite
  3. washThe celite was washed with EtOAc
  4. washthe combined organic phases were washed with brine (1×15 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-4b6c7c09a1144e5fb608d97c9ff36758
Source dataset
uspto-grants-2009_10
Patent number
US07598417B2

Reaction notes

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