Ethanol → HCID 22222222, compound

HRID 1794587Notes

Reaction equation

HRID 1794587 reaction equation
[CH2:1]([O:3][C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[C:6]([NH:8][N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]1[CH2:15][CH2:16][CH3:17])=[O:7])[CH3:2].[Br:22]Br.O.C(O)C>C(O)(=O)C.CC(C)=O>[Br:22][C:13]1[N:9]([NH:8][C:6](=[O:7])[C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]=2[O:3][CH2:1][CH3:2])[C:10]([CH2:15][CH2:16][CH3:17])=[N:11][C:12]=1[CH3:14]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24408BromineHCID 11414984HCID 11414984, compound

Product 1

HCID 22222222HCID 22222222, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 180AcetoneSolvent

Procedure

2-Ethoxy-N-(4-methyl-2-propylimidazol-1-yl)benzamide from Example D (50 g, 174 mmol) is introduced into acetic acid. Bromine (12.5 ml, 243.6 mmol) dissolved in acetic acid is added dropwise at room temperature. The mixture is then stirred at room temperature until conversion is complete (up to 3 hours). For working up, water and ethanol (or optionally acetone) are added to the mixture. The product is precipitated by neutralizing with sodium hydroxide solution. The crystals are isolated, washed and dried in vacuo.

Workup

  1. additionis added dropwise at room temperature
  2. custom(up to 3 hours)
  3. customThe product is precipitated by neutralizing with sodium hydroxide solution
  4. customThe crystals are isolated
  5. washwashed
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a7a4aecd6b924282a31f989da8b286d7
Source dataset
uspto-grants-2006_04
Patent number
US07022847B2

Reaction notes

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