Diisopropylethylamine → HCID 86629874, compound

HRID 1363739Notes

Reaction equation

HRID 1363739 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-diethyl-acetamide (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-d86d5a7ef9a847e58cf12010fd035fb2
Source dataset
uspto-grants-2011_02
Patent number
US07884210B2

Reaction notes

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