Ammonia → 3,5-Ditert-butyl-4-hydroxybenzamide

HRID 844490

반응식

HRID 844490 반응식
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8](O)=[O:9])([CH3:4])[CH3:3].[NH3:19]>O1CCCC1>[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([NH2:19])=[O:9])([CH3:4])[CH3:3]

참가 물질

4

반응물 2

HCID 222AmmoniaHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acid

생성물 1

HCID 6165023,5-Ditert-butyl-4-hydroxybenzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
26 °C

실험 절차

In a 22 L Morton flask, 749 g (3.0 mol) of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid, 533 g (3.3 mol) carbonylcuiimidazole and tetrahydrofuran (THF) were combined and heated slowly to reflux and allowed to reflux for 2.5 hours. The reaction mixture was cooled to 26° C. and concentrated aqueous ammonia was added. Stirring was continued for 2 hours and the reaction mixture was allowed to stand overnight. The contents were transferred to a flask and rinsed with tetrahydrofuran (250 mL). The mixture was stirred, layers were separated, and the aqueous layer was saved. The organic layer was washed with brine (2.5 L) followed by brine/deionized (DI) water (1 L/1.5 L). The organic layer was washed with 9.7 M hydrochloric acid (HCl)/deionized water (0.25 L/2.25 L), followed by 9.7 M hydrochloric acid/deionized water (0.5 L/2.8 L), and 9.7 M hydrochloric acid/deionized water/brine (0.5 L/1.5 L/1.5 L). The organic layer was set aside while the combined aqueous layers were washed with tetrahydrofuran. The combined organic layers were washed with brine, dried with sodium sulfate (855 g) and filtered. The filtrate was evaporated to 1011 g of a wet (water), white solid. Methylene chloride was added and removed in vacuo. This procedure was repeated with ethyl acetate (6 L, then 2 L) to produce a solid residue (779 g). The residue was slurried in ethyl acetate and heptane, filtered, and dried in a vacuum oven to yield the desired amide (736 g, 98.7%) as a white solid

후처리

  1. temperatureheated slowly
  2. temperatureto reflux
  3. temperatureto reflux for 2.5 hours
  4. waitto stand overnight
  5. customThe contents were transferred to a flask
  6. washrinsed with tetrahydrofuran (250 mL)
  7. stirringThe mixture was stirred
  8. customlayers were separated
  9. washThe organic layer was washed with brine (2.5 L)
  10. washThe organic layer was washed with 9.7 M hydrochloric acid (HCl)/deionized water (0.25 L/2.25 L)
  11. washwere washed with tetrahydrofuran
  12. washThe combined organic layers were washed with brine
  13. dry with materialdried with sodium sulfate (855 g)
  14. filtrationfiltered
  15. customThe filtrate was evaporated to 1011 g of a wet (water), white solid
  16. additionMethylene chloride was added
  17. customremoved in vacuo

출처 및 근거

ORD 기록
ord-1cb3c9919d0349e48b789298653ffa74
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380213B1

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