Nitric Acid → HCID 10613312, compound

HRID 1451096Notes

Reaction equation

HRID 1451096 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[N+:17]([O-])([OH:19])=[O:18]>O>[N+:17]([C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][C:6]=1[NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:10]([O:12][CH2:13][CH3:14])=[O:11])([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 250654ethyl 4-[(methylsulfonyl)amino]benzoate

Product 1

HCID 10613312HCID 10613312, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 4-[(methylsulfonyl)amino]benzoate (Lumma, W. C. et al. J. Med. Chem. 1987, 30, 758-763) (2.0 g, 0.0082 mol) was added portionwise to fuming nitric acid (10 mL) at 5°-10° C. over 0.25 h. The mixture was further stirred for 0.5 h at 10°-15° C. and then poured into cold water (50 mL). The yellow precipitate was separated by filtration and washed several times with cold water. The cake was recrystallized from ethyl acetate to give 1.7 g (72%) of ethyl 3-nitro-4-[(methylsulfonyl)amino]benzoate as yellow crystals, mp 124° C.

Workup

  1. customThe yellow precipitate was separated by filtration
  2. washwashed several times with cold water
  3. customThe cake was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-95b1ebc8c46c47bc95a85432ce397411
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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