Hydrochloric Acid → HCID 19848367, compound

HRID 1248110Notes

Reaction equation

HRID 1248110 reaction equation
N([O-])=O.[Na+].S(=O)(=O)(O)O.N[C:11]1[C:12]([Cl:24])=[C:13]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:14]([Cl:18])=[CH:15][C:16]=1[Cl:17].[Cu][C:26]#[N:27].[C-]#N.[K+].Cl>N.C(OCC)(=O)C.C(O)(=O)C>[C:26]([C:11]1[C:12]([Cl:24])=[C:13]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:14]([Cl:18])=[CH:15][C:16]=1[Cl:17])#[N:27]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 19848372HCID 19848372, compoundHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 19848367HCID 19848367, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 222AmmoniaSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

7 g of sodium nitrite is introduced under agitation at +5° C. into 84 ml of concentrated sulfuric acid. The mixture is stirred for another 10 minutes and then heated to 70° C. to obtain a clear solution. After cooling to 5° C., 42 ml of glacial acetic acid is added thereto under ice bath cooling. Then, 21.5 g of 3-(3-amino-2,4,6-trichlorophenyl)propionic acid is added in incremental portions at between 0° C. and +5° C., and the mixture is stirred for 2 hours at 5° C. The mixture is poured on 200 g of ice and thereafter, under agitation, is introduced into a solution of 35.4 g of copper(I) cyanide and 66.8 g of potassium cyanide in 900 ml of semiconcentrated ammonia; during this step, nitrogen is liberated. After stirring overnight at room temperature, 800 ml of ethyl acetate is added and the mixture is brought to pH 1 by dropwise addition of concentrated hydrochloric acid. After separating the precipitated inorganic salts by vacuum-filtering, the ethyl acetate phase is removed, washed twice with respectively 300 ml of water, and evaporated to dryness after drying over sodium sulfate. Recrystallization from seven times the amount of toluene yields 16 g (72% of theory) of 3-(3-cyano-2,4,6 -trichlorophenyl)propionic acid as a white powder, mp 127°-129° C.

Workup

  1. customto obtain a clear solution
  2. temperatureAfter cooling to 5° C.
  3. temperatureunder ice bath cooling
  4. stirringthe mixture is stirred for 2 hours at 5° C
  5. stirringAfter stirring overnight at room temperature
  6. customAfter separating the precipitated inorganic salts
  7. filtrationby vacuum-filtering
  8. customthe ethyl acetate phase is removed
  9. washwashed twice with respectively 300 ml of water
  10. customevaporated to dryness
  11. dry with materialafter drying over sodium sulfate
  12. customRecrystallization from seven times the amount of toluene

Sources & evidence

ORD record
ord-d6998a99a3184b72b918b007571c32f7
Source dataset
uspto-grants-1985_06
Patent number
US04522839

Reaction notes

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