Dimethylamine → N-[2-[4-oxocyclohexyl]ethyl] 2-propanesulfonamide

HRID 566476ノート

反応式

HRID 566476 の反応式
C(CC1C=CC([C:11]2[CH2:16][CH2:15][CH:14]([CH:17](C)CCC(S(N)(=O)=O)C)[CH2:13][CH:12]=2)=CC=1)(O)=O.S(Cl)(Cl)=[O:28].C[NH:32][CH3:33].[S:34](=[O:38])(=O)(O)[O-:35].[Na+].O1C[CH2:43][CH2:42][CH2:41]1>ClCCl>[O:28]=[C:11]1[CH2:12][CH2:13][CH:14]([CH2:17][CH2:33][NH:32][S:34]([CH:42]([CH3:43])[CH3:41])(=[O:38])=[O:35])[CH2:15][CH2:16]1

参加物

7

反応物 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 516919Sodium BisulfateHCID 867562312-[4-(4-Carboxymethylphenyl)-3-cyclohexen-1-yl]propyl 2-propanesulfonamide

生成物 1

HCID 22624691N-[2-[4-oxocyclohexyl]ethyl] 2-propanesulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 1 equivalent of N-[2-[4-(4-carboxymethylphenyl)-3-cyclohexen-1-yl]propyl 2-propanesulfonamide (see Example 31) in tetrahydrofuran is treated with 10 eq. of thionyl chloride and stirred at room temperature for 16 hours. The mixture is then concentrate in vacuo, dissolved in dichloromethane and added to a 0° C. solution of 1 eq. of dimethylamine in dichloromethane. The mixture is stirred at 0° C. for 2 hours. and 10% aqueous sodium bisulfate is added. The organic layer is separated and the aqueous layer is extracted two times with dichloromethane. The combined organic extracts are dried over NaSO4, filtered and concentrate in vacuo to provide the crude material. Chromatography of the crude material affords the title compound.

後処理

  1. concentrationThe mixture is then concentrate in vacuo
  2. dissolutiondissolved in dichloromethane
  3. stirringThe mixture is stirred at 0° C. for 2 hours
  4. customThe organic layer is separated
  5. extractionthe aqueous layer is extracted two times with dichloromethane
  6. dry with materialThe combined organic extracts are dried over NaSO4
  7. filtrationfiltered
  8. concentrationconcentrate in vacuo
  9. customto provide the crude material

出典と根拠

ORDレコード
ord-08b3e21c58dc48f085910346c298f3e0
出典データセット
uspto-grants-2001_01
特許番号
US06174922B1

反応ノート

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