Octane → HCID 19101410、化合物

HRID 1975258ノート

反応式

HRID 1975258 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].[CH3:16][N:17]([CH3:21])[C:18](Cl)=[S:19].CCCCCCCC.CCCCCC.C(OCC)(=O)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([Br:9])[C:7]=1[O:8][C:18](=[S:19])[N:17]([CH3:21])[CH3:16]

参加物

6

反応物 4

HCID 356OctaneHCID 27871Dimethylthiocarbamoyl chlorideHCID 318188Benzeneacetic acid, 3,5-dibromo-4-hydroxy-, ethyl esterHCID 21226206Ethyl acetate hexane

生成物 1

HCID 19101410HCID 19101410、化合物収率 62%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

Following the procedure of Newman and Karnes, J. Org. Chem. 31, 3980 (1966), a mixture of ethyl 3,5-dibromo-4-hydroxyphenylacetate (20 g, 0.06 mol), from Preparation B, N,N-dimethylthiocarbamoyl chloride (10.9 g, 0.088 mol), and 1,4-diazabicyclo[2 2.2]octane (Dabco™) (13.4 g, 0.12 mol) in 250 mL DMF was heated, with stirring, at 70° C. for one hour. The reaction mixture was cooled and the precipitate (Dabco-HCl salt) removed by filtration and washed well with ethyl acetate. The filtrate was concentrated on a rotary evaporator and the solid collected by filtration, washed well with water and dried in vacuum to obtain ethyl 3,5-dibromo-4-(N,N-dimethylthiocarbamoyloxy)phenylacetate (16 g, 0.037 mol, 62% yield), MP: 93°-95° C. (hexane/ethyl acetate).

後処理

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. customthe precipitate (Dabco-HCl salt) removed by filtration
  4. washwashed well with ethyl acetate
  5. concentrationThe filtrate was concentrated on a rotary evaporator
  6. filtrationthe solid collected by filtration
  7. washwashed well with water
  8. customdried in vacuum

出典と根拠

ORDレコード
ord-84d6524222c7406a8b1b89ce60433ba6
出典データセット
uspto-grants-1994_02
特許番号
US05284971

反応ノート

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