Benzene → HCID 44177176, compound

HRID 1673021Notes

Reaction equation

HRID 1673021 reaction equation
O[CH2:2][C:3]([NH:6][C:7]([C:9]1[N:10]=[C:11]([C:31]2[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:38])[N:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=3)=[CH:16][C:15]=2[Cl:30])[CH:13]=1)=O)([CH3:5])[CH3:4].C1C=CC=CC=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:46]>CCOC(C)=O>[Cl:30][C:15]1[CH:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=2)[CH:18]=[CH:19][C:14]=1[N:12]1[CH:13]=[C:9]([C:7]2[S:46][CH2:2][C:3]([CH3:5])([CH3:4])[N:6]=2)[N:10]=[C:11]1[C:31]1[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=1[Cl:38]

Participants

5

Reactant 3

HCID 241BenzeneHCID 14817Phosphorus sulfide (P2S5)HCID 59240454HCID 59240454, compound

Product 1

HCID 44177176HCID 44177176, compoundYield 17.2%

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′-methanesulfonyl-biphenyl-4-yl)-2-(2,6-dichloro-phenyl)-1H-imidazole-4-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (140 mg, 236 μmol), anhydrous benzene (14 mL) and P2S5 (500 mg, 2.25 mmol). The reaction solution was stirred at reflux for 1 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. The organic phase was partitioned, dried over Na2SO4, filtered, concentrated in vacuo, and chromatographed through a 25 g SiO2 column using a gradient of 100% Hexane to 80% EtOAc to afford 24 mg (17% yield) of title compound. MS (ESI) 590.0, 592.0, 594.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.27 (t, J=2 Hz, 1H), 8.21 (t, J=2 Hz, 1H), 8.17 (d, J=2 Hz, 1H), 8.14 (d, J=8 Hz, 1H), 8.10 (d, J=8 Hz, 1H), 7.99 (d, J=8 Hz, 1H), 7.95 (d, J=8 Hz, 1H), 7.78-7.85 (m, 2H), 7.74 (t, J=8 Hz, 1H), 7.49-7.61 (m, 3H), 7.43 (d, J=8 Hz, 1H), 3.36 (br s, 2H), 3.26 (s, 3H), 1.48 (s, 6H).

Workup

  1. customTo a N2 purged 50 mL round bottom flask
  2. customattached with condenser
  3. temperatureat reflux for 1 hr
  4. filtrationfiltered through a Buchner funnel
  5. customto remove excess P2S5
  6. washThe filtrate was washed with aq. 0.1 N NaOH
  7. customThe organic phase was partitioned
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customchromatographed through a 25 g SiO2 column

Sources & evidence

ORD record
ord-4963b50b51584ea2b0dc4098707b7666
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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