Sulfuric Acid → 3-Chloro-5-nitrotoluene

HRID 3136

반응식

HRID 3136 반응식
[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1N.S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[CH:3]=1

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 795952-Chloro-6-nitro-p-toluidineHCID 23668193Sodium Nitrite

생성물 1

HCID 2978873-Chloro-5-nitrotoluene수율 92%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a stirred mixture of 2-chloro-4-methyl-6-nitroaniline (7.39 g, 39.7 mM) and concentrated sulfuric acid (6.2 mL) in absolute ethanol (50 mL) at 0°-5° C. was slowly added a solution of sodium nitrite (6.85 g, 99.3 mM) in water (6 mL). The temperature of the reaction mixture was not allowed to exceed 5° C. during the addition. After the addition was completed, the reaction mixture was stirred at room temperature for 0.5 hr and then at reflux until the evolution of gas from the reaction mixture ceased. The reaction mixture was allowed to cool and was concentrated. The residue was slurried with ether and then filtered to remove the solids. The filtrate was concentrated and the residue chromatographed (eluant: diethyl ether/hexane; 1/9) to provide (6.25 g, 92%) the title compound as a yellow crystalline solid, mp 60.5-61° C.; MS(CI): 172 (M+H).

후처리

  1. additionto exceed 5° C. during the addition
  2. additionAfter the addition
  3. temperatureat reflux until the evolution of gas from the reaction mixture
  4. temperatureto cool
  5. concentrationwas concentrated
  6. filtrationfiltered
  7. customto remove the solids
  8. concentrationThe filtrate was concentrated
  9. customthe residue chromatographed (eluant: diethyl ether/hexane; 1/9)

출처 및 근거

ORD 기록
ord-b5beb2924d104c099a4a39902f3b9c14
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733910

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