Dimethylamine → HCID 178428583, compound

HRID 846277Notes

Reaction equation

HRID 846277 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][CH:33]=[CH:32][C:3]=1[C:4]([NH:6][C:7](=[N:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([Cl:29])=[CH:21][CH:20]=2)=[C:13]([Cl:30])[C:12]=1[CH3:31])SC)=[O:5].O1CCCC1.C(O)C.[CH3:44][NH:45][CH3:46]>O>[Cl:1][C:2]1[CH:35]=[CH:34][CH:33]=[CH:32][C:3]=1[C:4]([N:6]=[C:7]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([Cl:29])=[CH:21][CH:20]=2)=[C:13]([Cl:30])[C:12]=1[CH3:31])[N:45]([CH3:46])[CH3:44])=[O:5]

Participants

6

Reactant 4

HCID 674Dimethylamine2×HCID 702EthanolHCID 8028TetrahydrofuranHCID 136017127HCID 136017127, compound

Product 1

HCID 178428583HCID 178428583, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 5.0 grams of 1-(2-chlorobenzoyl)-3-[3-chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethylphenyl]-S-methylisothiourea prepared in Part A, 25 milliliters of tetrahydrofuran, 10 milliliters of ethanol and 50 milliliters of a 40% aqueous dimethylamine solution was refluxed in a nitrogen atmosphere for 5 hours. An additional 25 milliliters of 40% aqueous dimethylamine solution was added and reflux was continued for an additional 16 hours. After cooling to room temperature, the mixture was poured into 200 milliliters of water. This aqueous mixture was extracted twice with methylene chloride and twice with ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate. Removal of the solvents afforded 3.97 grams of a crude material. Chromatography of the crude material on silica gel using 9:1 ethyl acetate:methanol for elution afforded 1.87 grams of 2-(2-chlorobenzoyl)-3-[3-chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethylphenyl]-1, 1-dimethylguanidine as an amphomorous solid having a melting point of 85° C.-97° C. Elemental analysis of the amphomorous solid indicated the following:

Workup

  1. temperaturewas refluxed in a nitrogen atmosphere for 5 hours
  2. temperaturereflux
  3. extractionThis aqueous mixture was extracted twice with methylene chloride and twice with ethyl acetate
  4. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  5. customRemoval of the solvents
  6. customafforded 3.97 grams of a crude material
  7. washChromatography of the crude material on silica gel using 9:1 ethyl acetate:methanol for elution

Sources & evidence

ORD record
ord-b57a7d7194bf48ce88b43abb08ed3fcd
Source dataset
uspto-grants-1992_08
Patent number
US05135953

Reaction notes

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