Dimethylformamide → 6-chloro-3-(10-bromodecyl)-2H-1,3-benzoxazine-2,4(3H)-dione

HRID 456355

반응식

HRID 456355 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[NH:8][C:7](=[O:12])[C:6]=2[CH:13]=1.CN(C=O)C.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br.C(N(C(C)C)CC)(C)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[N:8]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][Br:19])[C:7](=[O:12])[C:6]=2[CH:13]=1

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 81531DiisopropylethylamineHCID 903596-Chloro-2h-1,3-benzoxazine-2,4(3h)-dioneHCID 2214831,10-Dibromodecane

생성물 1

HCID 222514226-chloro-3-(10-bromodecyl)-2H-1,3-benzoxazine-2,4(3H)-dione수율 49.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A slurry of 9.77 g of 6-chloro-2H-1,3-benzoxazine-2,4(3H)-dione (50 mmol) and 60 ml of DMF was treated with a solution of 1,10-dibromodecane (52.52 g, 0.175 mol) and DMF (60 ml) was added. Diisopropylethylamine (9.6 ml, 55 mmol) was added dropwise. A thermometer and condenser were attached, and the flask was placed in an oil bath. The reaction was heated to 60 C. for approximately 3 hrs, cooled to 47 C. and hexanes (150 ml) were added. The mixture was diluted with water (175 ml). The resulting solids were removed by filtration. The aqueous layer was washed with warm hexanes. The resulting solids were filtered from the hexane layer and recrystallized from warm hexanes to give 10.39 g of 6-chloro-3-(10-bromodecyl)-2H-1,3-benzoxazine-2,4(3H)-dione.

후처리

  1. additionwas added
  2. customthe flask was placed in an oil bath
  3. temperatureThe reaction was heated to 60 C
  4. temperaturecooled to 47 C
  5. customThe resulting solids were removed by filtration
  6. washThe aqueous layer was washed with warm hexanes
  7. filtrationThe resulting solids were filtered from the hexane layer
  8. customrecrystallized
  9. temperaturefrom warm hexanes

출처 및 근거

ORD 기록
ord-3eb9aa6ce62546f78904c2eb2703b578
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186414B2

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