Sulfuric Acid → HCID 19848351, compound

HRID 1608097Notes

Reaction equation

HRID 1608097 reaction equation
N([O-])=O.[Na+].S(=O)(=O)(O)O.N[C:11]1[C:12]([Br:24])=[C:13]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:14]([Br:18])=[CH:15][C:16]=1[Br:17].[Cu][C:26]#[N:27].[C-]#N.[K+].[Cl-].[Na+]>N.C(O)(=O)C>[C:26]([C:11]1[C:12]([Br:24])=[C:13]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:14]([Br:18])=[CH:15][C:16]=1[Br:17])#[N:27]

Participants

9

Reactant 6

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 9032Potassium CyanideHCID 19848358HCID 19848358, compoundHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 19848351HCID 19848351, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 222AmmoniaSolvent

Conditions

Temperature
70 °C

Procedure

3.5 g of sodium nitrite is introduced at 5° C. under agitation into 42 ml of concentrated sulfuric acid, stirred for 10 minutes,and then heated to 70° C. until a clear solution is obtained. After cooling to 5° C., 21 ml of glacial acetic acid is added under cooling in an ice bath. Then 16 g of 3-(3-amino-2,4,6-tribromophenyl)propionic acid is introduced in incremental portions between 0° C. and 5° C., and the mixture is agitated for 2 hours at 5° C. The mixture is poured on 200 g of ice and then under agitation is introduced into a solution of 18 g of copper(I) cyanide and 33.5 g of potassium cyanide in 450 ml of semiconcentrated ammonia, thus liberating nitrogen. The solution is saturated with sodium chloride and stirred overnight under water cooling. The thus-separated ammonium salt is vacuum-filtered and dissolved in the moist state in 200 ml of water. The solution is brought to pH 1 after treatment with activated carbon, by the addition of concentrated hydrochloric acid. After stirring for several hours in an ice bath, the precipitate is vacuum-filtered, washed with water, and dried at 50° C., thus producing 13 g (83% of theory) of 3-(3-cyano-2,4,6-tribromophenyl)propionic acid as a white powder, mp 164°-166° C.

Workup

  1. customis obtained
  2. temperatureAfter cooling to 5° C.
  3. temperatureunder cooling in an ice bath
  4. stirringthe mixture is agitated for 2 hours at 5° C
  5. stirringstirred overnight under water cooling
  6. filtrationThe thus-separated ammonium salt is vacuum-filtered
  7. dissolutiondissolved in the moist state in 200 ml of water
  8. additionby the addition of concentrated hydrochloric acid
  9. stirringAfter stirring for several hours in an ice bath
  10. filtrationthe precipitate is vacuum-filtered
  11. washwashed with water
  12. customdried at 50° C.

Sources & evidence

ORD record
ord-74c7326441604e99858f837e7227331a
Source dataset
uspto-grants-1989_09
Patent number
US04869913

Reaction notes

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