Carbon Dioxide → Win 54954

HRID 359848ノート

反応式

HRID 359848 の反応式
C(=O)([O-])[O-].[K+].[K+].Cl.[Cl:8][C:9]1[CH:14]=[C:13]([C:15]2[O:16][CH2:17][CH2:18][N:19]=2)[CH:12]=[C:11]([Cl:20])[C:10]=1[OH:21].C(=O)=O.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]1[O:35][N:34]=[C:33]([CH3:36])[CH:32]=1>CN(C)C=O>[Cl:8][C:9]1[CH:14]=[C:13]([C:15]2[O:16][CH2:17][CH2:18][N:19]=2)[CH:12]=[C:11]([Cl:20])[C:10]=1[O:21][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]1[O:35][N:34]=[C:33]([CH3:36])[CH:32]=1

参加物

6

反応物 4

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 135440465-(5-Bromopentyl)-3-methylisoxazoleHCID 1356214882,6-Dichloro-4-(4,5-dihydro-2-oxazolyl)phenol hydrochloride

生成物 1

HCID 441048Win 54954収率 60%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a stirred suspension of milled potassium carbonate (172.5 gm, 1.25 moles) in 1.35 L dimethylformamide (DMF) was added 2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenol hydrochloride (133.5 gm, 0.5 moles). Heavy gas evolution (CO2) occurred and the reaction was warmed on the steam bath to 70° C. After stirring for about 5 minutes, 5-(5-bromopentyl)-3-methylisoxazole (121.8 gm, 0.525 moles) was added in one portion. The mixture was heated to 90°-95° C. for 1 hr, allowed to cool to room temperature and then filtered. The filter cake was rinsed with DMF and the filtrate was concentrated under water vacuum to a viscous brown oil (260 gm). This residue was dissolved in 300 ml isopropyl acetate and washed with water and then with brine. The organic layer was dried over MgSO4, charcoaled, filtered and evaporated to dryness. The crude product (220 gm oil) was diluted with 287 ml acetone (1.5 volumes based on theoretical yield) and was cooled and stirred in a Dry Ice/acetone bath to -25° C. The product was collected and air dried to give 115 gm (60% yield) of 5-{5-[2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole, m.p. 38°-40° C. A sample when recrystallized from triethylamine had the m.p. 42°-43° C.

後処理

  1. temperatureThe mixture was heated to 90°-95° C. for 1 hr
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. washThe filter cake was rinsed with DMF
  5. concentrationthe filtrate was concentrated under water vacuum to a viscous brown oil (260 gm)
  6. dissolutionThis residue was dissolved in 300 ml isopropyl acetate
  7. washwashed with water
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness
  11. additionThe crude product (220 gm oil) was diluted with 287 ml acetone (1.5 volumes based on theoretical yield)
  12. temperaturewas cooled
  13. stirringstirred in a Dry Ice/acetone bath to -25° C
  14. customThe product was collected
  15. customair dried

出典と根拠

ORDレコード
ord-a7f0906bd32d42dbafbb8086068e8067
出典データセット
uspto-grants-1991_03
特許番号
US05002960

反応ノート

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