3-Chloroaniline → HCID 14492036, compound

HRID 2295946Notes

Reaction equation

HRID 2295946 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)N.[N+]([O-])([O-])=O.[Na+].C(=O)(O)[O-].[Na+].[SH:19][C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([S:19][C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 79323-ChloroanilineHCID 10340Sodium CarbonateHCID 24268Sodium NitrateHCID 516892Sodium BicarbonateHCID 178418793HCID 178418793, compound

Product 1

HCID 14492036HCID 14492036, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 3-chloroaniline (5.0 g) in 1.5 M hydrochloric acid (100 ml) was diazotised by the gradual addition of a solution of sodium nitrate (3.0 g) in water (6 ml) at 0° C. Sodium bicarbonate (7.5 g) was then added to the solution and the whole reaction mixture was added rapidly with stirring to a solution of 2-mercaptopyrimidine (4.5 g) in water (3 l). When the addition of the diazonium salt solution was completed, 10 ml of a 15% solution of sodium carbonate was added causing precipitation of a colourless solid. The solid was collected by filtration and allowed to stand overnight during which time it decomposed to an oil which was purified by chromatography (70 g silica, chloroform elution). The title compound was obtained as a red oil (2.5 g, 29%) and identified by its pmr spectrum.

Workup

  1. customthe whole reaction mixture
  2. additionwas added rapidly
  3. customprecipitation of a colourless solid
  4. filtrationThe solid was collected by filtration
  5. customwas purified by chromatography (70 g silica, chloroform elution)

Sources & evidence

ORD record
ord-77e8f4af98284c09839cabdc60dacf04
Source dataset
uspto-grants-1984_01
Patent number
US04427437

Reaction notes

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