Dimethyl Sulfide → HCID 19046449、化合物

HRID 1439935ノート

反応式

HRID 1439935 の反応式
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([Cl:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ClN1C(=O)CCC1=O.[CH3:21][S:22][CH3:23].C(N(CC)CC)C>ClCCl>[C:1]([C:5]1[CH:11]=[C:10]([CH2:21][S:22][CH3:23])[C:8]([NH2:9])=[C:7]([Cl:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 5210944-(Tert-Butyl)-2-Chloroaniline

生成物 1

HCID 19046449HCID 19046449、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-5 °C

実験手順

4-t-Butyl-2-chloroaniline (30 g) was dissolved in dichloromethane (1.21) and the solution was cooled to -5° C. N-chlorosuccinimide (21.7 g) was added portionwise to the vigorously stirred solution and stirring was continued for 1 h. Dimethyl sulfide (35 ml) was added to the solution (-5° C.) and stirring was continued for a further 1 h. The solution was then cooled to -65° C. and triethylamine (27 ml) was added. This solution was allowed to warm to room temperature overnight. The solution was evaporated to half volume, washed with sodium hydroxide (1N), water and brine successively. The organic solution was dried and evaporated and the residue was purified on silica using hexane to 3% ether in hexane as eluant. This afforded the product (31.2 g) as a red oil. 1H NMR (CDCl3, 250 MHz) δ 1.27 (9H, s, (CH3)3), 1.99 (3H, s, SCH3 ), 3.69 (2H, s, CH2SCH3), 4.38 (2H, br s, NH2), 6.92 (1H, d, J=2.0 Hz, ArH), 7.21 (1H, d, J=2.0 Hz, ArH). MS (CI+) m/z 244 (M+ +1, 100%).

後処理

  1. stirringstirring
  2. waitwas continued for a further 1 h
  3. temperatureThe solution was then cooled to -65° C.
  4. temperatureto warm to room temperature overnight
  5. customThe solution was evaporated to half volume
  6. washwashed with sodium hydroxide (1N), water and brine successively
  7. customThe organic solution was dried
  8. customevaporated
  9. customthe residue was purified on silica

出典と根拠

ORDレコード
ord-8ba57f399ec742878ffc403c0525a67b
出典データセット
uspto-grants-1996_03
特許番号
US05496833

反応ノート

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