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

HRID 2404800Notes

Reaction equation

HRID 2404800 reaction equation
[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]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 24437Sodium Sulfite2×HCID 8261032-Tert-butyl-5-nitroanilineHCID 23668193Sodium Nitrite

Product 1

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

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent3×

Conditions

Temperature
7.5 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-1c8c532c08aa4b6dac17fd06a7e16f87
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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