Hydrochloric Acid → HCID 14180973, compound

HRID 1722424Notes

Reaction equation

HRID 1722424 reaction equation
[ClH:1].Cl.[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)=[O:15])=[CH:9][CH:8]=1)(=[O:5])[CH3:4].Cl.[N:27]([O-])=O.[Na+]>O>[ClH:1].[C:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][NH2:27])=[CH:21][CH:20]=2)=[O:15])=[CH:11][CH:12]=1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14180971HCID 14180971, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14180973HCID 14180973, compoundYield 158.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The compound of Section (b) (6.25 g) was suspended in a mixture of water (17 ml) and concentrated hydrochloric acid (8.5 ml). The mixture was cooled in an ice bath and a solution of sodium nitrite (1.39 g) in water (8.5 ml) was added dropwise. The reaction mixture was stirred in the ice bath for 10 min to give a yellow solution with a fine suspension. The suspension was removed by filtration and the filtrate was collected in a cool receiver. The fltrate was poured into a solution of tin (II) chloride (20.6 g) in concentrated hydrochloric acid (8.5 ml) to give a yellow gum, which was removed and dissolved in ethanol (100 ml). The ethanol solution was evaporated in vacuo and re-evaporation with toluene gave a yellow gum. This gum was triturated with ER (250 ml) to give the title compound (9.36 g) as a pale yellow solid.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customto give a yellow solution with a fine suspension
  3. customThe suspension was removed by filtration
  4. customthe filtrate was collected in a cool receiver
  5. additionThe fltrate was poured into a solution of tin (II) chloride (20.6 g) in concentrated hydrochloric acid (8.5 ml)
  6. customto give a yellow gum, which
  7. customwas removed
  8. dissolutiondissolved in ethanol (100 ml)
  9. customThe ethanol solution was evaporated in vacuo and re-evaporation with toluene
  10. customgave a yellow gum
  11. customThis gum was triturated with ER (250 ml)

Sources & evidence

ORD record
ord-cbeb2848d5894278a794edbf006a3adb
Source dataset
uspto-grants-1989_08
Patent number
US04855314

Reaction notes

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