Hydrochloric Acid → 2-Tert-butyl-5-nitrobenzene-1-sulfonyl chloride

HRID 74075

반응식

HRID 74075 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1N)([CH3:4])([CH3:3])[CH3:2].N([O-])=O.[Na+].[O-:19][S:20]([O-:22])=O.[Na+].[Na+].[ClH:25]>O.[O-]S([O-])(=O)=O.[Cu+2]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[S:20]([Cl:25])(=[O:22])=[O:19])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric Acid2회HCID 24437Sodium Sulfite2회HCID 8261032-Tert-butyl-5-nitroanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 574702642-Tert-butyl-5-nitrobenzene-1-sulfonyl chloride수율 17%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 962Water용매3회

반응 조건

온도
7.5 °C

실험 절차

A suspension of 2-tert-butyl-5-nitrobenzenamine (0.971 g, 5 mmol) in conc. HCl (5 mL) was cooled to 5-10° C. and a solution of NaNO2 (0.433 g, 6.3 mmol) in H2O (0.83 mL) was added dropwise. Stirring was continued for 0.5 h, after which the mixture was vacuum filtered. The filtrate was added, simultaneously with a solution of Na2SO3 (1.57 g, 12.4 mmol) in H2O (2.7 mL), to a stirred solution of CuSO4 (0.190 g, 0.76 mmol) and Na2SO3 (1.57 g, 12.4 mmol) in HCl (11.7 mL) and H2O (2.7 mL) at 3-5° C. Stirring was continued for 0.5 h and the resulting precipitate was filtered off, washed with water and dried to give 2-tert-butyl-5-nitrobenzene-1-sulfonyl chloride (0.235 g, 17%). 1H NMR (400 MHz, DMSO-d6) δ 9.13 (d, J=2.5 Hz, 1H), 8.36 (dd, J=8.9, 2.5 Hz, 1H), 7.88 (d, J=8.9 Hz, 1H), 1.59 (s, 9H).

후처리

  1. filtrationfiltered
  2. stirringStirring
  3. waitwas continued for 0.5 h
  4. filtrationthe resulting precipitate was filtered off
  5. washwashed with water
  6. customdried

출처 및 근거

ORD 기록
ord-2e4511d4a9c04551b89c1886bcceef17
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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