Triethylamine → Ethyl 2-chloro-5-[(6-ethyl-2,3-dihydro-1,4-oxathiine-5-carbonyl)amino]benzoate

HRID 1938846ノート

反応式

HRID 1938846 の反応式
S(Cl)(Cl)=O.[CH2:5]([C:7]1[O:8][CH2:9][CH2:10][S:11][C:12]=1[C:13]([OH:15])=O)[CH3:6].[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([Cl:28])=[C:21]([CH:27]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(N(CC)CC)C>C(Cl)Cl.C(O)C>[Cl:28][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:13]([C:12]2[S:11][CH2:10][CH2:9][O:8][C:7]=2[CH2:5][CH3:6])=[O:15])=[CH:27][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 13226857Ethyl 5-amino-2-chlorobenzoateHCID 214702502-Ethyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid

生成物 1

HCID 465810Ethyl 2-chloro-5-[(6-ethyl-2,3-dihydro-1,4-oxathiine-5-carbonyl)amino]benzoate収率 58%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
35 °C

実験手順

Thionyl chloride (4.0 g, 0.034 mole) was added to a stirred mixture of 2-ethyl-5,6-dihydro-1,4-oxathiin-3-carboxylic acid (5.9 g, 0.034 mole) and methylene chloride (100 ml). The mixture was warmed to about 35° C. for 3 hours, then evaporated under reduced pressure. The residue, crude 2-ethyl-5,6-dihydro-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (100 ml), and the ice-chilled solution treated dropwise with a solution of ethyl 5-amino-2-chlorobenzoate (6.8 g, 0.034 mole) and triethylamine (3.7 g, 0.037 mole) in methylene chloride (100 ml). The reaction mixture was stirred overnight at room temperature and then worked up by washing in sequence with water, dilute hydrochloric acid, water, 2% sodium hydroxide and water. Evaporation of the solvent left an oil, which solidified. After recrystallization from ethanol (30 ml) the product (7.0 g, 58% yield) melted at 86°-88° C.

後処理

  1. customevaporated under reduced pressure
  2. dissolutionThe residue, crude 2-ethyl-5,6-dihydro-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (100 ml)
  3. temperaturethe ice-chilled solution
  4. washby washing in sequence with water, dilute hydrochloric acid, water, 2% sodium hydroxide and water
  5. customEvaporation of the solvent
  6. waitleft an oil, which

出典と根拠

ORDレコード
ord-a1c15475bb674007b50fa2fd9847a27e
出典データセット
uspto-grants-1997_12
特許番号
US05693827

反応ノート

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