Methyl iodide → HCID 20255167, compound

HRID 638035Notes

Reaction equation

HRID 638035 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([N:14]([CH2:35][CH2:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[C:40]([C:52](=[O:54])[NH2:53])[CH:39]=1)[CH2:15][CH:16]([OH:34])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[NH:26][CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:29]=2)=[CH:21][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CI>CN(C)C=O>[CH2:7]([N:14]([CH2:35][CH2:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[C:40]([C:52](=[O:54])[NH2:53])[CH:39]=1)[CH2:15][CH:16]([OH:34])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:26]([CH3:1])[CH:27]=[C:28]([C:30]([F:31])([F:32])[F:33])[N:29]=2)=[CH:21][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178513693HCID 178513693, compound

Product 1

HCID 20255167HCID 20255167, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

At 0°, 0.18 g of potassium tert.-butoxide is added to a solution of 1.0 g of 1-[N-benzyl-2-(3-carbamoyl-4-benzyloxyphenoxy)-ethylamino]-3-[4-[4-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol in 5 ml of dimethylformamide and the mixture is stirred for 20 minutes in an ice bath. At 0°-5°, a solution of 0.12 ml of methyl iodide in 3 ml of dimethylformamide is added and the mixture is then stirred for 4 hours at room temperature. The reaction solution is concentrated by evaporation, the residue is dissolved in water and the solution is extracted with ethyl acetate. After drying the organic phase over sodium sulphate, this is concentrated to dryness by evaporation, yielding the crude 1-[N-benzyl-2-(3-carbamoyl-4-benzyloxyphenoxy)-ethylamino]-3-[4-[1-methyl-4-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol which is further processed in that form.

Workup

  1. stirringthe mixture is then stirred for 4 hours at room temperature
  2. concentrationThe reaction solution is concentrated by evaporation
  3. dissolutionthe residue is dissolved in water
  4. extractionthe solution is extracted with ethyl acetate
  5. dry with materialAfter drying the organic phase over sodium sulphate
  6. concentrationthis is concentrated to dryness by evaporation

Sources & evidence

ORD record
ord-c3aaab5e4d324943b814f6571d72483c
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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