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

HRID 470112Notes

Reaction equation

HRID 470112 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-a972d52ab52c4159bc0079472afd58f8
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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