Sodium Methoxide → N,N-diethyl 2-amino-4-methylthiazole-5-sulfonamide

HRID 618196Notes

Reaction equation

HRID 618196 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[S:4]([C:7]1[S:11][C:10]([NH:12]C(=O)C)=[N:9][C:8]=1[CH3:16])(=[O:6])=[O:5])[CH3:2].C[O-].[Na+]>CO.O>[CH2:17]([N:3]([CH2:1][CH3:2])[S:4]([C:7]1[S:11][C:10]([NH2:12])=[N:9][C:8]=1[CH3:16])(=[O:6])=[O:5])[CH3:18]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 21850614N,N-diethyl 2-acetamido-4-methylthiazole-5-sulfonamide

Product 1

HCID 21850461N,N-diethyl 2-amino-4-methylthiazole-5-sulfonamideYield 22.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

The product from Step 1 (2.5 g) was dissolved in methanol (25 cm3) and cooled to 5° C. with stirring under an atmosphere of nitrogen. Sodium methoxide in methanol (2 cm3 of 25% wt./vol. solution) was added dropwise and the mixture allowed to warm to the ambient temperature for 18 hours. The reaction was heated under reflux for 1 hour, cooled, diluted with water (250 cm3), extracted with diethyl ether (2×100 cm3), dried (MgSO4) and evaporated under reduced pressure to give N,N-diethyl 2-amino-4-methylthiazole-5-sulfonamide (0.48 g). M+ 249; 1H NMR: δ 1.20(6H,t); 2.48(3H,s); 3.28(4H,q); 5.25(2H,br s); (solid).

Workup

  1. temperatureto warm to the ambient temperature for 18 hours
  2. temperatureThe reaction was heated
  3. temperatureunder reflux for 1 hour
  4. temperaturecooled
  5. extractionextracted with diethyl ether (2×100 cm3)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cfa97ec3df174ccaa7ab27d05a8877b3
Source dataset
uspto-grants-1999_09
Patent number
US05952359

Reaction notes

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