Sulfuric Acid → HCID 58760944, compound

HRID 857483Notes

Reaction equation

HRID 857483 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[C:10]=1[CH:11]=[CH:12][O:13]C)=[O:5])[CH3:2].OS(O)(=O)=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[N:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[C:10]=1[CH2:11][CH:12]=[O:13])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 69411264HCID 69411264, compound

Product 1

HCID 58760944HCID 58760944, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 2-(4-chloro-phenyl)-1-(2-chloro-phenyl)-5-(2-methoxy-vinyl)-1H-imidazole-4-carboxylic acid ethyl ester I-5g (275 mg, 0.659 mmol) and H2SO4 (200 μl) in 5:1 THF/H2O (18 ml) was heated at 70° C. for 3 hours. The reaction mixture was cooled to room temperature and treated with 1M K2CO3 until the pH of the reaction mixture was ˜6. The aqueous solution was extracted with CH2Cl2 and the combined organic extracts were washed with sat'd aq. NaCl, dried, and concentrated in vacuo to give a mixture of the starting material and product (I-5h): +APCI MS (M+1) 403.3

Workup

  1. extractionThe aqueous solution was extracted with CH2Cl2
  2. washthe combined organic extracts were washed with sat'd aq. NaCl
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give
  6. additiona mixture of the starting material and product (I-5h)

Sources & evidence

ORD record
ord-81ac8416af69492dbbe6d696e8c1ddb1
Source dataset
uspto-grants-2006_12
Patent number
US07145012B2

Reaction notes

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