Benzene → HCID 44177499, compound

HRID 1673033Notes

Reaction equation

HRID 1673033 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:29]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([C:13]([NH:15][C:16]([CH3:20])([CH3:19])[CH2:17]O)=O)[N:10]=[C:9]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27].C1C=CC=CC=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:45]>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:29]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([C:13]2[S:45][CH2:17][C:16]([CH3:20])([CH3:19])[N:15]=2)[N:10]=[C:9]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27]

Participants

5

Reactant 3

HCID 241BenzeneHCID 14817Phosphorus sulfide (P2S5)HCID 59240051HCID 59240051, compound

Product 1

HCID 44177499HCID 44177499, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a N2 purged 50 mL round bottom flask attached with condenser was added 1-(3-chloro-3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-chlorophenyl)-N-(1-hydroxy-2-methyl propan-2-yl)-1H-imidazole-4-carboxamide (361 mg, 646 μmol), anhydrous benzene (20 mL) and P2S5 (720 mg, 3.24 mmol). The reaction solution was stirred at reflux for 1.5 hr. The reaction solution was diluted with EtOAc (100 mL) and filtered through a Buchner funnel to remove excess P2S5. The filtrate was washed with aq. 0.1 N NaOH (60 mL) and H2O (100 mL). The partitioned organic phase was dried over Na2SO4, filtered, concentrated in vacuo, and chromatographed through a 12 g SiO2 column using a gradient of 100% hexane to 95% EtOAc to afford 68 mg (19% yield) of title compound. MS (ESI) 556.3, 558.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 8.10 (t, J=2.0 Hz, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.83 (d, J=8.0 Hz, 1H), 7.79 (br s, 1H), 7.66-7.70 (m, 2H), 7.55 (d, J=7.2 Hz, 1H), 7.43 (dd, J1 8.5=Hz, J2=2.0 Hz, 1H), 7.27-7.33 (m, 4H), 3.22 (s, 2H), 3.10 (s, 3H), 1.51 (s, 6H).

Workup

  1. customTo a N2 purged 50 mL round bottom flask
  2. customattached with condenser
  3. temperatureat reflux for 1.5 hr
  4. filtrationfiltered through a Buchner funnel
  5. customto remove excess P2S5
  6. washThe filtrate was washed with aq. 0.1 N NaOH (60 mL) and H2O (100 mL)
  7. dry with materialThe partitioned organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customchromatographed through a 12 g SiO2 column

Sources & evidence

ORD record
ord-e3f30d190755411f9931401e6aff0a9a
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

Loading…