Hydrochloric Acid → HCID 20391937, compound

HRID 1863494Notes

Reaction equation

HRID 1863494 reaction equation
Cl.[Cl:2][C:3]1[C:10]([N+:11]([O-])=O)=[C:9]([Cl:14])[C:8]([N+:15]([O-])=O)=[CH:7][C:4]=1[C:5]#[N:6].[OH-].[Na+]>>[Cl:2][C:3]1[C:10]([NH2:11])=[C:9]([Cl:14])[C:8]([NH2:15])=[CH:7][C:4]=1[C:5]#[N:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 987512,4-Dichloro-3,5-dinitrobenzonitrile

Product 1

HCID 20391937HCID 20391937, compound

Procedure

A solution of 330 g. (1.46 mole) of stannous chloride dihydrate in 807 ml. of concentrated hydrochloric acid is stirred and there is added 53.5 gm. (0.204 mole) of 2,4-dichloro-3,5-dinitrobenzonitrile. The temperature rises to 85° and is then allowed to cool to room temperature over a period of two hours. The mixture is cooled to 5° in an ice-bath and there is added, slowly, 50% sodium hydroxide until the mixture is strongly basic. The precipitate is removed by filtration. The filtrate is placed in a separatory funnel. The precipitate is extracted with three volumes of ethyl acetate. The combined ethyl acetate extracts are added to the aqueous filtrate and the resulting mixture shaken thoroughly for ten minutes. The phases are separated and the organic phase dried over magnesium sulfate. The drying agent is removed by filtration. The filtrate is evaporated to dryness in vacuo. The yellow solid is recrystallized from absolute ethanol to yield 33.7 g. (82%) of yellow needles melting at 189°-191°.

Workup

  1. additionthere is added 53.5 gm
  2. customrises to 85°
  3. temperatureThe mixture is cooled to 5° in an ice-bath
  4. additionthere is added
  5. customThe precipitate is removed by filtration
  6. customThe filtrate is placed in a separatory funnel
  7. extractionThe precipitate is extracted with three volumes of ethyl acetate
  8. additionThe combined ethyl acetate extracts are added to the aqueous filtrate
  9. customThe phases are separated
  10. dry with materialthe organic phase dried over magnesium sulfate
  11. customThe drying agent is removed by filtration
  12. customThe filtrate is evaporated to dryness in vacuo
  13. customThe yellow solid is recrystallized from absolute ethanol
  14. customto yield 33.7 g

Sources & evidence

ORD record
ord-98dce8eac3f44289a7db4a8b255ceee0
Source dataset
uspto-grants-1979_09
Patent number
US04169153

Reaction notes

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