Hydrochloric Acid → HCID 20329637, compound

HRID 2057976Notes

Reaction equation

HRID 2057976 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:17][C:16]=3[CH:25]=2)=[CH:8][CH:7]=1.[ClH:26]>O>[Cl:26][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:17][C:16]=3[CH:25]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20329649HCID 20329649, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20329637HCID 20329637, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 6.9 g of sodium nitrite in 40 ml of water was added drop-by-drop to a stirred mixture of 30 g of 12C and 160 ml of 6 N hydrochloric acid, the rate of addition being adjusted to maintain the temperature of the reaction mixture at 0°-5° C. The mixture was stirred for 1 hour at 0°-5° C., then added with vigorous stirring, to 50 ml of 20% aqueous cuprous chloride heated to 70° C. The resulting mixture was heated to 70° C., then allowed to cool. The solid was collected, washed with water, dried (P2O5, reduced pressure) and dissolved in tetrahydrofuran. The solution was suspended on 75 g of silica gel and dry column chromatographed, using chloroform as eluent. The product was removed from the combined appropriate fractions with tetrahydrofuran. The solvent was evaporated ad the residue was dried (drying pistol, P2O5, refluxing acetone) to give ethyl 5-(4-chlorophenyl)benzofuran-2-carboxylate (12 D), mp 108°-110° C.

Workup

  1. additionthe rate of addition
  2. temperatureto maintain the temperature of the reaction mixture at 0°-5° C
  3. temperatureThe resulting mixture was heated to 70° C.
  4. temperatureto cool
  5. customThe solid was collected
  6. washwashed with water
  7. dry with materialdried (P2O5, reduced pressure)
  8. dissolutiondissolved in tetrahydrofuran
  9. customdry column
  10. customchromatographed
  11. customThe product was removed from the combined appropriate fractions with tetrahydrofuran
  12. customThe solvent was evaporated ad the residue
  13. customwas dried
  14. dry with material(drying pistol, P2O5, refluxing acetone)

Sources & evidence

ORD record
ord-8c19123f1a7040ed974c22866ebeb5bc
Source dataset
uspto-grants-1980_07
Patent number
US04213998

Reaction notes

Loading…