Propionic Acid → HCID 178504818, compound

HRID 46423Notes

Reaction equation

HRID 46423 reaction equation
[CH3:1][S:2]([C:5]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:6]=1[NH2:7])(=[O:4])=[O:3].C(O)(=O)CC.N([O-])=O.[Na+].[NH:24]1[C:28]2[CH:29]=[CH:30][C:31]([NH:33][C:34]([C:36]3C=C[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=3)=[O:35])=[CH:32][C:27]=2[N:26]=[N:25]1.[C:46]([O-:49])(=O)[CH3:47].[NH4+:50]>S(=O)(=O)(O)O.C(O)(=O)C>[NH:24]1[C:28]2[CH:29]=[CH:30][C:31]([NH:33][C:34]([C:36]3[CH:37]=[C:38]([N:50]=[N:7][C:6]4[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=4[S:2]([CH3:1])(=[O:4])=[O:3])[C:39]4[C:47](=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:46]=3[OH:49])=[O:35])=[CH:32][C:27]=2[N:26]=[N:25]1

Participants

8

Reactant 5

HCID 1032Propionic Acid2×HCID 667852-Mesyl-4-nitroanilineHCID 517165Ammonium AcetateHCID 23668193Sodium NitriteHCID 178521834HCID 178521834, compound

Product 1

HCID 178504818HCID 178504818, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

2-Methylsulphonyl-4-nitroaniline (0.66 g) was diazotized in a mixture of 3:1 v/v glacial acetic acid:propionic acid (40 ml) by adding sodium nitrite (0.21 g) in concentrated sulphuric acid (2.5 ml) dropwise a 0° C. The resulting diazonium solution was added to N-(benzotriazol-5-yl)naphth-2-amide (1.0 g) dissolved in 3:1 v/v glacial acetic acid:propionic acid (100 ml) containing ammonium acetate (16.2 g) and the mixture was stirred at room temperature for one hour. The mixture was poured onto ice and the product was filtered and crystallized in aqueous pyridine. Yield 1.16 g, m.p. 260° decomp., λmax (methanol)=577 nm.

Workup

  1. additionThe mixture was poured onto ice
  2. filtrationthe product was filtered
  3. customcrystallized in aqueous pyridine

Sources & evidence

ORD record
ord-78ab3763dcfc4510b7ddb2ca398e2a43
Source dataset
uspto-grants-1979_11
Patent number
US04173478

Reaction notes

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