Sodium Nitrite → HCID 22168599, compound

HRID 635401Notes

Reaction equation

HRID 635401 reaction equation
NC1C=C(C=C([N+]([O-])=O)C=1)C(O)=O.[CH3:14][S:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[CH:24]=1)[C:19]([OH:21])=[O:20].N([O-])=O.[Na+]>S(=O)(=O)(O)O.O>[CH3:14][S:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[CH:24]=1)[C:19]([OH:21])=[O:20]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 86756414HCID 86756414, compound

Product 1

HCID 22168599HCID 22168599, compoundYield 180.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

3-Methylthio-5-nitrobenzoic acid 3-Amino-5-nitrobenzoic acid (1.82 g, 10 mM) was dissolved in concentrated sulphuric acid (1.9 ml), diluted with water (10 ml), and cooled to 5°. A solution of NaNO2 (0.7 g, 10 mM) in water (3 ml) was added and the mixture stirred for 30 minutes. The cold solution of diazonium salt was added to a slurry of thiomethylcopper(I) at 3°, and the mixture stirred for 45 minutes. Organics were extracted into ethyl acetate (5×60 ml), and the combined organic layers washed with aqueous NaH2PO4, water, brine, and dried over Na2SO4. Evaporation gave 3-methylthio-5-nitrobenzoic acid (1.77 g, 83%). Nmr (DMSO-d6): δ 2.63 (s, 3H); 8.10 (t, 1H); 8.21 (t, 1H); 8.32 (t, 1H); 13.68 (br, 1H).

Workup

  1. temperaturecooled to 5°
  2. stirringthe mixture stirred for 45 minutes
  3. extractionOrganics were extracted into ethyl acetate (5×60 ml)
  4. washthe combined organic layers washed with aqueous NaH2PO4, water, brine
  5. dry with materialdried over Na2SO4
  6. customEvaporation

Sources & evidence

ORD record
ord-7163aa1dde16425f96f9d1f8d00a75ae
Source dataset
uspto-grants-2001_02
Patent number
US06187804B1

Reaction notes

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