Dimethylamine → HCID 13881300, compound

HRID 1906912Notes

Reaction equation

HRID 1906912 reaction equation
[OH:1][CH:2]([CH3:21])[CH2:3][NH:4][S:5]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:9]=1[C:10]([O:12]C)=O)(=[O:7])=[O:6].C[O-].[Na+].[CH3:25][NH:26][CH3:27]>CO>[CH3:25][N:26]([CH3:27])[C:10](=[O:12])[C:9]1[C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=[CH:17][C:8]=1[S:5]([NH:4][CH2:3][CH:2]([OH:1])[CH3:21])(=[O:6])=[O:7]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 10942334Sodium MethoxideHCID 13881295HCID 13881295, compound

Product 1

HCID 13881300HCID 13881300, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 2-[N-(2-hydroxy-1-propyl)aminosulfonyl]-6-nitrobenzoate (2.00g, 628 mmol) was dissolved in 60 ml of methanol. Sodium methoxide (1.0 ml of a 0.1 M solution in methanol) was added and the solution cooled and stirred in an ice-bath while a rapid stream of dimethylamine was passed into the vortex for 15 minutes. Stirring in the ice-bath then was continued for 1 hour, when the flash was removed from the bath and the reaction mixture allowed to stand at room temperature overnight. The methanol and excess dimethylamine then were evaporated under reduced pressure and the residue shaken with ethyl acetate, 80 ml; 0.2N HCl, 10 ml; and saturated NaCl, 10 ml. The ethyl acetate layer was separated, extracted with 3×15 ml of saturated NaCl and evaporated to give a clear yellow oil. After drying 23 hours in vacuo, this product weight 2.03 g. Crystallization had started after 3 days. Recrystallization from a mixture of ethyl acetate and hexane gave 1.33 g (63.9%) of product, m.p., 95.5°-97°.

Workup

  1. temperaturethe solution cooled
  2. waitthen was continued for 1 hour
  3. customwhen the flash was removed from the bath
  4. waitto stand at room temperature overnight
  5. customThe methanol and excess dimethylamine then were evaporated under reduced pressure
  6. customThe ethyl acetate layer was separated
  7. extractionextracted with 3×15 ml of saturated NaCl
  8. customevaporated
  9. customto give a clear yellow oil
  10. customAfter drying 23 hours in vacuo
  11. customCrystallization
  12. waithad started after 3 days
  13. customRecrystallization
  14. additionfrom a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-6bbc6303b1244fe2962905f487a75b3b
Source dataset
uspto-grants-1987_03
Patent number
US04654369

Reaction notes

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