Hydrochloric Acid → HCID 14051162, compound

HRID 1199696Notes

Reaction equation

HRID 1199696 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)/[CH:5]=[CH:6]/[C:7]1[S:8][C:9]([CH3:14])=[C:10]([CH2:12][CH3:13])[N:11]=1.Cl.N([O-])=[O:20].[Na+]>O>[OH:20][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)/[CH:5]=[CH:6]/[C:7]1[S:8][C:9]([CH3:14])=[C:10]([CH2:12][CH3:13])[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14051192HCID 14051192, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14051162HCID 14051162, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An amount of 3.0 g of 2-(trans-3-aminostyryl)-4-ethyl-5-methylthiazole was added to 18 ml of 20% hydrochloric acid and to the mixture was added dropwise slowly 3 ml of an aqueous solution of 0.86 g of sodium nitrite while maintaining the inner temperature at 4° to 5° C. After the mixture was stirred at the above temperature for 1.5 hours, the reaction mixture was added into 50 ml of boiling water over 20 minutes. After the mixture was cooled to room temperature, the precipitates formed were collected by filtration, washed with aqueous saturated sodium hydrogen carbonate solution and with water, followed by drying under reduced pressure. The crude product was washed with toluene and dried under reduced pressure to obtain 2.1 g (yield 70%) of the title compound.

Workup

  1. temperaturewhile maintaining the inner temperature at 4° to 5° C
  2. customthe precipitates formed
  3. filtrationwere collected by filtration
  4. washwashed with aqueous saturated sodium hydrogen carbonate solution and with water
  5. customby drying under reduced pressure
  6. washThe crude product was washed with toluene
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-46cbba8021a743108ee7098df99ccf9c
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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