Dimethylamine → 3-(5,5-Dimethyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-1,1-dimethyl-urea

HRID 595080

反応式

HRID 595080 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][C:8]([CH3:13])([CH3:12])[CH2:7][C:5]=2[N:6]=1.C1N=[CH:17][N:16]([C:19](N2C=NC=C2)=[O:20])[CH:15]=1.C1CCN2C(=NCCC2)CC1.CNC>C(#N)C>[CH3:12][C:8]1([CH3:13])[CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:19](=[O:20])[N:16]([CH3:17])[CH3:15])[S:3][C:4]=2[C:10](=[O:11])[CH2:9]1

参加物

6

反応物 4

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5878742-Amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one

生成物 1

HCID 205043303-(5,5-Dimethyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-1,1-dimethyl-urea収率 82.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one (151 g, 0.768 mol) in acetonitrile (5 L) are added CDI (249 g, 1.53 mol) and DBU (233 g, 1.53 mol). The reaction mixture is stirred overnight at 100° C. Dimethylamine (310 g, 3.83 mol) is added at RT and the stirring is continued overnight at 100° C. After cooling to RT, the reaction mixture is concentrated in vacuo and the residue is poured into ice water. The pH of the mixture is adjusted to pH 5 with HCl (6 M). The aqueous mixture is extracted with ethyl acetate (4×500 mL). The combined organic layers are washed with brine (500 mL) and dried over anhydrous Na2SO4. The solvent is evaporated in vacuo to give crude product. The crude product is washed with water to give 3-(5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-1,1-dimethyl-urea (169 g, 82% yield).

後処理

  1. waitthe stirring is continued overnight at 100° C
  2. temperatureAfter cooling to RT
  3. concentrationthe reaction mixture is concentrated in vacuo
  4. additionthe residue is poured into ice water
  5. extractionThe aqueous mixture is extracted with ethyl acetate (4×500 mL)
  6. washThe combined organic layers are washed with brine (500 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent is evaporated in vacuo
  9. customto give crude product
  10. washThe crude product is washed with water

出典と根拠

ORDレコード
ord-6999cae8d4f342d0ae16606ad2a34978
出典データセット
uspto-grants-2016_01
特許番号
US09243000B2

関連ノート

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