Hydrochloric Acid → HCID 178432289, compound

HRID 2423306Notes

Reaction equation

HRID 2423306 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:31][C:32]([O:34]C)=[O:33])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])(=[O:22])=[O:21])=[CH:17][C:12]2[N:13]=[C:14]([CH3:16])[NH:15][C:11]=2[CH:10]=1.[Li+].[OH-].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:31][C:32]([OH:34])=[O:33])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])(=[O:21])=[O:22])=[CH:17][C:12]2[N:13]=[C:14]([CH3:16])[NH:15][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178499463HCID 178499463, compound

Product 1

HCID 178432289HCID 178432289, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an N2 atmosphere, methyl 2-(3-chloro-4-(6-(2,4-dichlorophenylsulfonamido)-2-methyl-3H-benzo[d]imidazol-5-yloxy)phenyl)acetate (0.138 g, 0.248 mmol) was dissolved in THF (2.5 mL), and 1N LiOH (2.5 mL) was added. The reaction was allowed to stir at room temperature for 2.5 h. The reaction was brought to pH 5 with 1N HCl and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated with an ethyl acetate/hexanes mixture and the product was collected by filtration. LC-MS ESI (pos.) m/z: 541.9 (M+H). 1H NMR (400 MHz) (DMSOd-6) δ 7.76 (d, J=8.5 Hz, 1H); 7.64 (d, J=1.8 Hz, 1H); 7.62 (s, 1H), 7.43-7.40 (m, 2H); 7.10 (d, J=8.2 Hz, 1H); 6.77 (s, 1H); 6.57 (d, J=8.3 Hz, 1H); 3.59 (s, 2H); 2.61 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with an ethyl acetate/hexanes mixture
  6. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-79ef9e84b6be4a979e510857319f4f45
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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