Hydrochloric Acid → HCID 9892218, compound

HRID 2298232Notes

Reaction equation

HRID 2298232 reaction equation
C[O:2][C:3](=[O:28])[C:4]([NH:6][C:7]1[CH:12]=[C:11]([Br:13])[C:10]([O:14][C:15]2[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[C:18]([OH:24])=[CH:17][C:16]=2[CH2:25][CH3:26])=[C:9]([Br:27])[CH:8]=1)=[O:5].[OH-].[Na+].Cl>CC(C)=O>[CH2:25]([C:16]1[CH:17]=[C:18]([OH:24])[C:19]([CH:21]([CH3:22])[CH3:23])=[CH:20][C:15]=1[O:14][C:10]1[C:9]([Br:27])=[CH:8][C:7]([NH:6][C:4](=[O:5])[C:3]([OH:28])=[O:2])=[CH:12][C:11]=1[Br:13])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9936321HCID 9936321, compound

Product 1

HCID 9892218HCID 9892218, compoundYield 718.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(4-(2-ethyl-4-hydroxy-5-isopropylphenoxy)-3,5-dibromophenyl)oxamic acid methyl ester (50 mg, 0.01 mmol), was dissolved in acetone (2 ml). 1M NaOH (1 ml) was added and the solution was stirred for 1 hour, cooled in an ice bath, acidified with 1M HCl, concentrated, extracted with ethyl acetate, dried over MgSO4, filtered and evaporated to give 36 mg (74%) of N-(4-(2-ethyl-4-hydroxy-5-isopropylphenoxy)-3,5-dibromophenyl)oxamic acid. 1H NMR (CD3COCD3): d 10.24 (s, 1H), 8.33 (s, 2H), 6.77 (s, 1H), 6.12 (s, 1H), 3.16 (m, 1H), 2.74 (q, 2H), 1.27 (t, 3H), 1.04 (d, 6H).

Workup

  1. temperaturecooled in an ice bath
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a402a3c6f42e46a3beb10a3b72430912
Source dataset
uspto-grants-2002_12
Patent number
US06492424B1

Reaction notes

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