Water → Acetamide, N-[5-[(4-methyl-1-piperazinyl)sulfonyl]-2-thiazolyl]-

HRID 1685535Notes

Reaction equation

HRID 1685535 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([S:11](Cl)(=[O:13])=[O:12])=[C:8](C)[N:9]=1)(=[O:3])[CH3:2].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.O>C(Cl)Cl>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([S:11]([C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][CH:8]=2)(=[O:13])=[O:12])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 531671-MethylpiperazineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chloride

Product 1

HCID 42560673Acetamide, N-[5-[(4-methyl-1-piperazinyl)sulfonyl]-2-thiazolyl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-acetamido-4-methyl-5-thiazolesulfonyl chloride (3 g, 11.8 mmol) in DCM (50 mL) and TEA (3.2 mL, 23.6 mmol) was slowly added N-methylpiperazine (1.2 g, 12.4 mmol). The reaction mixture was stirred at room temperature for 2 hours. Water (50 mL) was added, and the organic phase was isolated. The water phase was extracted with DCM (3×75 mL). The combined organic phase was dried with anhydrous magnesium sulphate, filtered, and evaporated in vacuo to give 2.6 g of yellow, impure crystals. Purification on a silica gel column (Eluent: DCM:MeOH (9:1)) gave N-[5-(4-methylpiperazine-1-sulfonyl)-thiazol-2-yl]-acetamide as light yellow crystals of N-[5-(4-methylpiperazine-1-sulfonyl)-thiazol-2-yl]-acetamide. Yield: 1.52 g (41%). 1H-NMR (CDCl3): δ3.20 (m, 4H); 2.55 (m, 7H); 2.32 (s, 3H); 2.29 (s, 3H).

Workup

  1. customthe organic phase was isolated
  2. extractionThe water phase was extracted with DCM (3×75 mL)
  3. dry with materialThe combined organic phase was dried with anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give 2.6 g of yellow, impure crystals
  7. customPurification on a silica gel column (Eluent: DCM:MeOH (9:1))

Sources & evidence

ORD record
ord-db5a0791042f44dbbea53fd4229182e8
Source dataset
uspto-grants-2012_04
Patent number
US08148412B2

Reaction notes

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