Diethylamine → N,N-diethyl 2-acetamido-4-methylthiazole-5-sulfonamide

HRID 618195Notes

Reaction equation

HRID 618195 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([S:11](Cl)(=[O:13])=[O:12])=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[CH2:15]([NH:17][CH2:18][CH3:19])[CH3:16]>O1CCCC1>[CH2:15]([N:17]([CH2:18][CH3:19])[S:11]([C:7]1[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=1[CH3:10])(=[O:13])=[O:12])[CH3:16]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (5.2 g) in tetrahydrofuran (100 cm3) was stirred at ambient temperature and treated portionwise with diethylamine (4.5 cm3). The mixture was stirred for 4 hours, evaporated under reduced pressure and the residue extracted into ethyl acetate (200 cm3), washed with water (2×100 cm3), dried (MgSO4) and re-evaporated under reduced pressure to give N,N-diethyl 2-acetamido-4-methylthiazole-5-sulfonamide (4.9 g). 1H NMR: δ 1.20(6H,t); 2.28(3H,s); 2.57(3H,s); 3.32(4H,q); 9.7(1H,br s); (solid).

Workup

  1. customevaporated under reduced pressure
  2. extractionthe residue extracted into ethyl acetate (200 cm3)
  3. washwashed with water (2×100 cm3)
  4. dry with materialdried (MgSO4)
  5. customre-evaporated under reduced pressure

Sources & evidence

ORD record
ord-4713e573c9c748ecaefd43c3b069468b
Source dataset
uspto-grants-1999_09
Patent number
US05952359

Reaction notes

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