Sodium Hydroxide → HCID 57437746, compound

HRID 857479Notes

Reaction equation

HRID 857479 reaction equation
[Br:1]Br.[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH:12]=1)=[O:7])[CH3:4].[OH-].[Na+]>C(O)(=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:12]=1[Br:1])=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 22285380HCID 22285380, compound

Product 1

HCID 57437746HCID 57437746, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (3.6 ml, 0.07 mol) was added to a solution of 1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester (I-5c, 3.6 g, 0.01 mol) in glacial acetic acid (50 ml) at room temperature. The reaction mixture was stirred for 17 hours, poured over ice-water, and treated with 25% aq. NaOH until the orange solution turned yellow. The aqueous solution was extracted with CH2Cl2 (3×) and the combined extracts were dried and concentrated in vacuo to give the desired compound I-5d as an oil (4.7 g): +APCI MS (M+1) 441.1; 1H NMR (CD3Cl) δ 1.41 (3H, t), 4.43 (2H, q), 7.08–7.12 (2H, m), 7.20–7.40 (7H, m).

Workup

  1. extractionThe aqueous solution was extracted with CH2Cl2 (3×)
  2. customthe combined extracts were dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff09c900f67c4d90933182d2fdd5d512
Source dataset
uspto-grants-2006_12
Patent number
US07145012B2

Reaction notes

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