Water → HCID 66682832, compound

HRID 530294Notes

Reaction equation

HRID 530294 reaction equation
CO.C(=O)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:29])[C:14]([N:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=3)[N:18]=[CH:17]2)=[O:15])=[CH:9][CH:8]=1.O>ClCCl>[F:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]([CH3:29])[C:14]([N:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[N:18]=[CH:17]2)=[O:15])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21973728Carbon dioxide methanolHCID 66682190HCID 66682190, compound

Product 1

HCID 66682832HCID 66682832, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an methanol-dry ice cooled solution of N-(4-fluorophenyl)-4-(4-methoxyphenyl)-N-methyl-1H-imidazole-1-carboxamide (0.283 g, 0.870 mmol) in dichloromethane (8 ml) was added borontribromide (0.164 ml, 1.740 mmol). The dark reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. TLC showed the reaction to be completed, then was poured into a mixture of ice and water and stirred for 30 min. There was no precipitation. The mixture was extracted with DCM:IPA (70:30), the organic phase was dried over MgSO4 and filtered. DCM was removed by vacuum and the product precipitated from IPA, filtered and dried under vacuum. (Yield: 210 mg, 78%).

Workup

  1. customThe dark reaction mixture
  2. customthe reaction
  3. stirringstirred for 30 min
  4. customno precipitation
  5. extractionThe mixture was extracted with DCM:IPA (70:30)
  6. dry with materialthe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. customDCM was removed by vacuum
  9. customthe product precipitated from IPA
  10. filtrationfiltered
  11. customdried under vacuum

Sources & evidence

ORD record
ord-f72d4a846d8a4a3082315873da955b42
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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