Hydrochloric Acid → 6-Chloro-2h-1,3-benzoxazine-2,4(3h)-dione

HRID 19443

反応式

HRID 19443 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].N1C=CC=CC=1.Cl[C:19](OCC)=[O:20].Cl>O.C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:19](=[O:20])[NH:9][C:7](=[O:8])[C:6]=2[CH:10]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 3480945-Chloro-2-hydroxybenzamide

生成物 1

HCID 903596-Chloro-2h-1,3-benzoxazine-2,4(3h)-dione収率 85.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
95 °C

実験手順

A solution of 10 g of 5-chloro-2-hydroxybenzamide (58.0 mmol), pyridine (22 ml) and acetonitrile (25 ml) was stirred in an ice bath. Ethyl chloroformate (6.1 ml, 0.0638 mol) was added dropwise. The pink solution was stirred for 30 minutes at <10° C. The ice bath was replaced with an oil bath. The reaction mixture was heated to 95° C. and the volatiles were distilled off (43 ml). The reaction was cooled to room temperature, causing a white solid to form. The mixture was poured into water (100 ml) and acidified with concentrated aqueous hydrochloric acid. The resulting solid was filtered and recrystallized in hot ethanol to give 9.77 g of 6-chloro-2H-1,3-benzoxazine-2,4(3H)-dione.

後処理

  1. distillationthe volatiles were distilled off (43 ml)
  2. temperatureThe reaction was cooled to room temperature
  3. customto form
  4. filtrationThe resulting solid was filtered
  5. customrecrystallized in hot ethanol

出典と根拠

ORDレコード
ord-d1b5b65db5a349c791c13059ce7ef66b
出典データセット
uspto-grants-2010_06
特許番号
US07744910B2

関連ノート

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