Sodium Hydroxide → N-BENZO[1,3]DIOXOL-5-YL-2-CHLORO-PROPIONAMIDE

HRID 1462016Notes

Reaction equation

HRID 1462016 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.[OH-].[Na+].[Cl:13][CH:14]([CH3:18])[C:15](Cl)=[O:16]>C(Cl)(Cl)Cl>[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH:6][C:15](=[O:16])[CH:14]([Cl:13])[CH3:18])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 843101,3-Benzodioxol-5-amineHCID 1110192-Chloropropionyl chloride

Product 1

HCID 4174537N-BENZO[1,3]DIOXOL-5-YL-2-CHLORO-PROPIONAMIDE

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3,4-methylenedioxyaniline, (41.1 grams; 0.3 moles) in 270 cc of chloroform containing 90 cc of a 20% solution of sodium hydroxide, there is added 38.1 grams (0.3 moles) of 2-chloropropionyl chloride at about -10° C., while stirring vigorously and keeping the temperature not above -5° C. The mixture is stirred for an additional period of one hour, letting the temperature reach room temperature. The organic phase is then separated, washed with water, neutralized with potassium carbonate and allowed to evaporate at reduced pressure, thus obtaining a solid purplish residue from which the desired product is separated and recrystallized with diisopropyl ether with melting point 116°-117° C.; Rf=0.26 (toluene-AcOEt 9:1) I.R. (nujol) νmax: 3240, 1660, 1540, 1500, 1485, 1445, 1250, 1210, 1040, 930, 815, 790 cm-1 ; chlorine (Schoeninger) calc. % 15.6--Found % 15.5.

Workup

  1. customthe temperature not above -5° C
  2. stirringThe mixture is stirred for an additional period of one hour
  3. customreach room temperature
  4. customThe organic phase is then separated
  5. washwashed with water
  6. customto evaporate at reduced pressure

Sources & evidence

ORD record
ord-f1dc160d6e484841bb9a469cdf51e3e3
Source dataset
uspto-grants-1984_07
Patent number
US04457931

Reaction notes

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