Reaktion #161257

Reaktionsgleichung

Na2SO3

Na2SO3

HCl

NaNO2

2-tert-butyl-5-nitrobenzenamine

HCl

→

2-tert-butyl-5-nitrobenzene-1-sulfonyl chloride

Ausbeute 17.0%

Lösungsmittel

H2O

H2O

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITwas continued for 0.5 h
4. 4
   Filtrationthe resulting precipitate was filtered off
5. 5
   Waschenwashed with water
6. 6
   Sonstigedried

Vorschrift

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).

Quelle