Dimethylamine → HCID 15907985, compound

HRID 1268040Notes

Reaction equation

HRID 1268040 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[S:30])[NH:13][C:14]2[CH:27]=[C:26]([Cl:28])[C:17]([O:18][CH2:19][CH2:20]OS(C)(=O)=O)=[C:16]([Cl:29])[CH:15]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:31][NH:32][CH3:33]>O1CCCC1.C(OCC)(=O)C>[Cl:28][C:26]1[CH:27]=[C:14]([NH:13][C:12](=[S:30])[NH:11][C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)[CH:15]=[C:16]([Cl:29])[C:17]=1[O:18][CH2:19][CH2:20][N:32]([CH3:33])[CH3:31]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 12019007HCID 12019007, compound

Product 1

HCID 15907985HCID 15907985, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methanesulfonic acid 2-{4-[3-(4-acetylamino-phenyl)-thioureido]-2,6-dichlorophenoxy}-ethyl ester (0.33 g) in tetrahydrofuran (6 mL) is added aqueous dimethyl-amine (8.8 M, 0.5 mL) and the mixture is stirred at room temperature for 5 days. The reaction mixture is then diluted with ethyl acetate, then washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure the residue is chromatographed over silica gel (pure methanol is used as the eluant). Pooled product containing fractions are evaporated under reduced pressure and the residue is recrystallized from acetonitrile to provide the desired product as a white powder.

Workup

  1. washwashed with saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter removal of the solvent under reduced pressure the residue
  4. customis chromatographed over silica gel (pure methanol
  5. additionPooled product containing fractions
  6. customare evaporated under reduced pressure
  7. customthe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-3ac58aff7f7f4bf1a18f6d4daae7cb2d
Source dataset
uspto-grants-2003_04
Patent number
US06555561B2

Reaction notes

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