Dichloromethane → 1H-Imidazole-4-sulfonamide, 1-methyl-N-(3-(4-morpholinyl)propyl)-

HRID 1708160

Reaction equation

HRID 1708160 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([S:7](Cl)(=[O:9])=[O:8])[N:4]=[CH:3]1.[O:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][NH2:20])[CH2:13][CH2:12]1.ClCCl>C(#N)C>[O:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][NH:20][S:7]([C:5]2[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=2)(=[O:9])=[O:8])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 61055N-(3-Aminopropyl)morpholineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chloride

Product 1

HCID 30714701H-Imidazole-4-sulfonamide, 1-methyl-N-(3-(4-morpholinyl)propyl)-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 30 g (0.17 mol) of 1-methylimidazole-4-sulfonyl chloride from Example C-1 in 150 ml of acetonitrile is added dropwise to a solution of 24 ml (0.17 mol) of 3-morpholinopropylamine in 50 ml of acetonitrile (or dichloromethane). The temperature of the reaction mixture is kept at room temperature or below by external cooling with ice-water. Stirring is continued for 6 h at room temperature. The precipitate deposited is filtered off with suction and recrystallized from acetonitrile in order to give 46 g (85% of theory) of the title compound (hydrochloride) of melting point 207°-208° C.

Workup

  1. customis kept at room temperature or below
  2. filtrationThe precipitate deposited is filtered off with suction
  3. customrecrystallized from acetonitrile in order

Sources & evidence

ORD record
ord-517e471b01a5402590d8508386022272
Source dataset
uspto-grants-1994_10
Patent number
US05356922

Linked notes

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