Hydrochloric Acid → HCID 54022387, compound

HRID 839424Notes

Reaction equation

HRID 839424 reaction equation
[CH2:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].Cl[CH2:13][C:14]([O-:16])=[O:15].[Na+].[OH-:18].[Na+].Cl.[O:21]1[CH2:26][CH2:25]OCC1>O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([N:9]([CH2:25][C:26]([OH:21])=[O:18])[CH2:13][C:14]([OH:16])=[O:15])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 76944-ButylanilineHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 23665759Sodium chloroacetate

Product 1

HCID 54022387HCID 54022387, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Into a three-neck r.b. flask, equipped with glass stirrer, reflux condenser, thermometer, and addition funnel were placed 29.9g (0.2M) p-n-butylaniline; 46.6g (0.4M) sodium chloroacetate dissolved in a solution of 200 ml water and 45 ml dioxane and 10 drops of a mixed acid/base indicator. The solution was heated to reflux and a solution of 16g sodium hydroxide in 64 ml water was added dropwise so as to maintain the pH between 5 and 8 as shown by the indicator. Reaction was completed within 4 hours. The reaction mixture upon dilution with 500 ml water and cooling was acidified with 43 ml conc. hydrochloric acid. The formed precipitate was filtered and washed twice with 200 ml of water at pH 1.3 and dried under vacuum at 40° C. Yield: 41.2g beige solids (%N = 4.9.)

Workup

  1. customflask, equipped with glass stirrer
  2. temperaturereflux condenser
  3. additionthermometer, and addition funnel
  4. temperatureThe solution was heated
  5. temperatureto reflux
  6. temperatureto maintain the pH between 5 and 8
  7. customReaction
  8. filtrationThe formed precipitate was filtered
  9. washwashed twice with 200 ml of water at pH 1.3
  10. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-2e5ce51751604849bdcc0178f879ad5d
Source dataset
uspto-grants-1978_06
Patent number
US04095019

Reaction notes

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