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Water → 2-Amino-4-methyl-3,5-dinitrobenzamide

HRID 968785
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HRID 968785 반응식
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[NH2:17]N1C=NN=C1.CC(C)([O-])C.[K+].O>CS(C)=O.C(O)(=O)C>[NH2:17][C:9]1[C:10]([N+:11]([O-:13])=[O:12])=[C:2]([CH3:1])[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]=1[C:6]([NH2:8])=[O:7]
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참가 물질

7

반응물 4

HCID 962WaterHCID 114324-Amino-1,2,4-triazole2회HCID 33186984-Methyl-3,5-dinitrobenzamideHCID 23665647Potassium tert-butoxide2회

생성물 1

HCID 590163082-Amino-4-methyl-3,5-dinitrobenzamide수율 84.4%

시약·촉매·용매 2

HCID 176
Acetic Acid
용매
HCID 679Dimethyl Sulfoxide용매2회

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온도
20 °C

실험 절차

A solution of 4-methyl-3,5-dinitrobenzamide (6) (15.1 kg) in dimethyl sulfoxide (95.6 kg) is added to a solution of 4-amino-1,2,4-triazole (21.6 kg) and potassium tert-butoxide (21.7 kg) in dimethyl sulfoxide (144.5 kg) at a rate to maintain a temperature of about 20° C. The mixture is allowed to stir for about 30 minutes, whereupon additional amounts of 4-amino-1,2,4-triazole (5.5 kg) and potassium tert-butoxide (3.7 kg) are added. The mixture is allowed to stir for about 1 hour at about 20° C., and then the mixture is added, over a period of about 30 minutes, to a cold (about 5° C.) solution of water (347 kg) and acetic acid (15 kg), allowing the temperature to rise to about 25° C. The vessel containing the initial reaction mixture is then rinsed with water (87 kg) and the rinse solution is also added to the acetic acid solution. The resulting mixture is cooled to about 5° C. and held at this temperature for about 30 minutes, whereupon the mixture is filtered and the solids obtained are washed with water (82 kg). The solids are then dried in a vacuum tray dryer for about 19 hours, at a temperature of about 50° C. and a vacuum of about 15 torr, to provide 2-amino-4-methyl-3,5-dinitrobenzamide (7) (13.6 kg, 84% yield).

후처리

  1. additionare added
  2. customto rise to about 25° C
  3. additionThe vessel containing the initial
  4. customreaction mixture
  5. washis then rinsed with water (87 kg)
  6. additionthe rinse solution is also added to the acetic acid solution
  7. temperatureThe resulting mixture is cooled to about 5° C.
  8. waitheld at this temperature for about 30 minutes, whereupon the mixture
  9. filtrationis filtered
  10. customthe solids obtained
  11. washare washed with water (82 kg)
  12. customThe solids are then dried in a vacuum tray dryer for about 19 hours, at a temperature of about 50° C.

출처 및 근거

ORD 기록
ord-13067bd3f02f49a8927a515e6ad212e1
출처 데이터셋
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07304084B2

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