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

HRID 19443

반응식

HRID 19443 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d1b5b65db5a349c791c13059ce7ef66b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07744910B2

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