Hydrochloric Acid → HCID 67288797, compound

HRID 1626495Notes

Reaction equation

HRID 1626495 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:33])[NH:20][C:21]3[CH:22]=[N:23][N:24]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=4)[CH:25]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:34]([O:36]CC)=[O:35].[OH-].[Na+].Cl>O1CCCC1.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:33])[NH:20][C:21]3[CH:22]=[N:23][N:24]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=4)[CH:25]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:34]([OH:36])=[O:35]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67288044HCID 67288044, compound

Product 1

HCID 67288797HCID 67288797, compoundYield 103%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Ethyl 6-chloro-7-(4-(1-(3-chlorophenyl)-1H-pyrazol-4-ylcarbamoyl)phenoxy)chroman-4-carboxylate (280 mg, 0.5 mmol) was dissolved in 2:1 tetrahydrofuran/ethanol (3 mL) and treated with sodium hydroxide (2 ml of a 1 N solution, 2.0 mmol) at ambient temperature. After 3 hours, the reaction was diluted with water (20 mL), acidified with 2N HCl (2 mL) and extracted with ethyl acetate. The combined organic phases were dried (sodium sulfate), filtered and the solvent removed under vacuum to provide the title compound (270 mg, 102%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried (sodium sulfate)
  3. filtrationfiltered
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-5cecc09da7a148d180ebdea0d963bff1
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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