Water → Acetamide, N-[4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-

HRID 916563Notes

Reaction equation

HRID 916563 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([S:11]([C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)(=[O:13])=[O:12])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 531671-Methylpiperazine

Product 1

HCID 764494Acetamide, N-[4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-Yield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-acetylaminobenzene sulfonyl chloride (4.5 mmol) in anhydrous CH2Cl2 at room temperature is treated with 1-methyl piperazine (4.5 mmol) and triethylamine (4.5 mmol). The reaction mixture was stirred at room temperature for 1 hour, water was added, and the product extracted with additional CH2Cl2. The combined organic extracts were dried (Na2SO4), filtered, and evaporated under reduced pressure, affording the desired N-[4-(4-methylpiperazine-1-sulfonyl)phenyl]acetamide. Mp: 184° C.; Yield 41%; 1H NMR (DMSO d6): δ 2.09 (s, 3H), 2.15 (s, 3H), 2.40 (m, 4H), 2.85 (m, 4H), 7.63-7.68 (d,2H, J=10 Hz), 7.80-7.84 (d, 2H, J=8 Hz), 10.41 (s, 1H).

Workup

  1. extractionthe product extracted with additional CH2Cl2
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d577b767647e468c891e2fe101832c28
Source dataset
uspto-grants-2007_09
Patent number
US07271171B2

Reaction notes

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