Triethylamine → HCID 86607106, compound

HRID 900881Notes

Reaction equation

HRID 900881 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[C:7]([NH:10][C:11]1[S:12][C:13]([S:17](Cl)(=[O:19])=[O:18])=[C:14]([CH3:16])[N:15]=1)(=[O:9])[CH3:8].C(N(CC)CC)C>O1CCCC1>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][S:17]([C:13]1[S:12][C:11]([NH:10][C:7](=[O:9])[CH3:8])=[N:15][C:14]=1[CH3:16])(=[O:18])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chloride

Product 1

HCID 86607106HCID 86607106, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N,N-dimethylethylenediamine (1.04 g, 11.8 mmol) in tetrahydrofurane (14 ml) was added at 0° C. (ice water bath) commercially available 2-acetamido-4-methylthiazole-5-sulfonyl chloride (1.0 g, 3.93 mmol) and triethylamine (0.6 ml, 4 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1) and subsequent crystallization (dichloromethane/hexane) to yield 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-dimethylamino-ethyl)-amide (1.07 g, 89%) as a white solid. MS (ISP) 305.1 [(M−H)−]; mp 143° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1) and subsequent crystallization (dichloromethane/hexane)

Sources & evidence

ORD record
ord-53e078dad0a94090b00ee258068c4f73
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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