Diisopropylethylamine → HCID 86629874, compound

HRID 2043923Notes

Reaction equation

HRID 2043923 reaction equation
[CH2:1]([N:3]([CH2:9][CH3:10])[C:4](=[O:8])[CH2:5][NH:6][CH3:7])[CH3:2].[C:11]([NH:14][C:15]1[S:16][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:18][N:19]=1)(=[O:13])[CH3:12].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:11]([NH:14][C:15]1[S:16][C:17]([S:20]([N:6]([CH3:7])[CH2:5][C:4]([N:3]([CH2:9][CH3:10])[CH2:1][CH3:2])=[O:8])(=[O:21])=[O:22])=[CH:18][N:19]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3502612-Acetamido-1,3-thiazole-5-sulfonyl chlorideHCID 2543180HCID 2543180, compound

Product 1

HCID 86629874HCID 86629874, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of N,N-diethyl-2-methylamino-acetamide (12 mmol), 2-acetylamino-thiazole-5-sulfonyl chloride (12 mmol) (prepared as described in J. Am. Chem. Soc 69, 2063, 1947), DIPEA (15 mmol) in DCM (50 mL) was stirred at room temperature over night. The reaction mixture was diluted with DCM (50 mL) washed with 10% aq NaHSO4, water and brine, dried and concentrated to give 2-[(2-acetylamino-thiazole-5-sulfonyl)-methyl-amino]-N,N-diethylacetamide (59%) as pale yellow crystals. This was suspended in EtOH (10 mL) and added 8N HCl in dioxane (10 mL) and heated for 3H at 80° C. and then cooled to room temperature and concentrated in vacuo to give 2-[(2-amino-thiazole-5-sulfonyl)-methyl-amino]-N,N-diethyl-acetamide as a hydrochloride as colourless crystals.

Workup

  1. washwashed with 10% aq NaHSO4, water and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4c182d12c2574086b98ca9d19a896de9
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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