Hydrochloric Acid → 5-Carboxy-2,1,3-benzoxadiazol-1-ium-1-olate

HRID 1890442

반응식

HRID 1890442 반응식
[OH-:1].[K+].[NH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[N+:13]([O-:15])=O.Cl[O-].[Na+].Cl.[Na+].[Cl-]>C(O)C.O.C(O)(=O)C.CC(C)=O.C(Cl)(Cl)Cl>[N+:3]1([O-:1])[O:15][N:13]=[C:5]2[CH:6]=[C:7]([C:8]([OH:10])=[O:9])[CH:11]=[CH:12][C:4]=12

참가 물질

11

반응물 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 23665760Sodium Hypochlorite

생성물 1

HCID 3352815-Carboxy-2,1,3-benzoxadiazol-1-ium-1-olate수율 88.8%

시약·촉매·용매 5

HCID 176Acetic Acid용매HCID 180Acetone용매HCID 702Ethanol용매HCID 962Water용매2회HCID 6212Chloroform용매

반응 조건

온도
67.5 °C

실험 절차

In a 3 L reactor fitted with mechanical stirring, reflux condenser, thermometer and nitrogen inlet, KOH (72.46 g) was dissolved in ethanol (250 ml) and water (250 ml). 4-Amino-3-nitrobenzoic acid (100 g) was added and the orange suspension was heated to 65-70° C. within 30 minutes. The resulting suspension was stirred at the same temperature for 45 minutes and cooled to 0° C.±5° C. within 30 minutes. A commercially available (13% w/w) solution of sodium hypochlorite (448.93 g) was added drop wise within 1.5 hours at 0° C.±5° C. The reaction mixture was stirred at the same temperature for 2 hours and controlled by TLC (CHCl3 100/acetone 2/acetic acid 1). Water (350 ml) was added within 15 minutes at 0° C.±5° C. to give a fine yellow suspension. The reaction mixture was then acidified with a 6N HCl solution (239 ml) until 0.5<pH<1 was reached. NaCl (58.44 g) was added and the resulting suspension was stirred at 0° C.±5° C. for 1.5 hours under nitrogen. The solid was collected by filtration, washed with 3×400 ml water and dried (40° C., 30 mbars, 12 hours) to yield 83.6 g (88.8% yield) of [2,1,3]-benzoxadiazole-5-carboxylic acid N-oxide.

후처리

  1. customIn a 3 L reactor fitted with mechanical stirring
  2. temperaturereflux condenser
  3. temperaturecooled to 0° C.±5° C. within 30 minutes
  4. stirringThe reaction mixture was stirred at the same temperature for 2 hours
  5. customto give a fine yellow suspension
  6. stirringthe resulting suspension was stirred at 0° C.±5° C. for 1.5 hours under nitrogen
  7. filtrationThe solid was collected by filtration
  8. washwashed with 3×400 ml water
  9. customdried (40° C., 30 mbars, 12 hours)

출처 및 근거

ORD 기록
ord-36895df67edb484daf3183fa34af1187
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507482B2

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