Hydrochloric Acid → HCID 59864781, compound

HRID 2423302Notes

Reaction equation

HRID 2423302 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:42][C:43]([O:45]C)=[O:44])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:29]=[CH:28][C:12]2[N:13](S(C3C=CC(Cl)=CC=3Cl)(=O)=O)[C:14]([CH3:16])=[N:15][C:11]=2[C:10]=1[NH:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=1[Cl:41])(=[O:33])=[O:32].[Li+].[OH-].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:42][C:43]([OH:45])=[O:44])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:29]=[CH:28][C:12]2[NH:13][C:14]([CH3:16])=[N:15][C:11]=2[C:10]=1[NH:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=1[Cl:41])(=[O:32])=[O:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59864816HCID 59864816, compound

Product 1

HCID 59864781HCID 59864781, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Under an N2 atmosphere, methyl 2-(3-chloro-4-(4-(2,4-dichlorophenylsulfonamido)-1-(2,4-dichlorophenylsulfonyl)-2-methyl-1H-benzo[d]imidazol-5-yloxy)phenyl)acetate (0.097 g, 0.127 mmol) was dissolved in tetrahydrofuran (1.5 mL) and 1 N LiOH (1.5 mL) was added. The reaction was stirred at 50° C. for 3 h. The reaction was diluted with water, made acidic with 1N HCl to pH 4, and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to afford the title compound. LC-MS ESI (pos.) m/z: 541.9 (M+H). 1H NMR (400 MHz) (DMSOd-6) δ 7.63 (d, J=8.5 Hz, 1H); 7.46 (bs, 1H); 7.31-7.22 (m, 3H); 6.94 (d, J=7.6 Hz, 1H); 6.46 (bs, 1H); 6.29 (bs, 1H) 3.51 (s, 2H); 2.48 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c2fb3cee49334def97594ff3b958b3d5
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

Loading…