Triethylamine → 2,3,4-Trifluorophenyl isothiocyanate

HRID 1722068ノート

反応式

HRID 1722068 の反応式
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=S)[S-:12].C([NH+](CC)CC)C.C(N(CC)CC)C.C(Cl)(=O)OCC>C(Cl)(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[N:10]=[C:11]=[S:12]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16413959N,N-diethyl-1-ethanaminium N-(2,3,4-trifluorophenyl)carbamodithioate

生成物 1

HCID 27607912,3,4-Trifluorophenyl isothiocyanate収率 78.3%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Triethylammonium N-(2,3,4-trifluorophenyl)dithiocarbamate (92.0 g) and triethylamine (31.5 g) were added to chloroform (360 ml) and thereto ethyl chlorocarbonate (33.8 g) was added dropwise at 2°-6° C. with stirring over a period of 1 hour. The mixture was stirred for 10 minutes and washed with 3N hydrochloric acid and then with water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The obtained residue ws purified by silica-gel column chromatography (Silica gel 60, 230-400 mesh, made by Merck Co., 220 g, eluent: hexane) under medium pressure, followed by distillation under reduced pressure to give the title compound (42.0 g) as colorless liquid, b.p.: 96°-97° C./17 mmHg.

後処理

  1. stirringThe mixture was stirred for 10 minutes
  2. washwashed with 3N hydrochloric acid
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue ws purified by silica-gel column chromatography (Silica gel 60, 230-400 mesh, made by Merck Co., 220 g, eluent: hexane) under medium pressure
  6. distillationfollowed by distillation under reduced pressure

出典と根拠

ORDレコード
ord-7d8e24dd8e8f4bd58c2b55f9106626b2
出典データセット
uspto-grants-1989_08
特許番号
US04853469

反応ノート

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