Dimethylformamide → HCID 53739999, compound

HRID 1252691Notes

Reaction equation

HRID 1252691 reaction equation
[N:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:16][CH2:17][CH:18]=[CH:19][CH2:20]Cl.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C1(C)C=CC=CC=1>[Cl:16][CH2:17][CH:18]=[CH:19][CH2:20][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 151221,4-Dichloro-2-buteneHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazole

Product 1

HCID 53739999HCID 53739999, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(1-piperazinyl)-1,2-benzisothiazole (1 g; 4.56 mmol), 1,4-dichloro-2-butene (2.9 g; 22.8 mmol), anhydrous potassium carbonate (0.79 g; 5.7 mmol) and dry dimethylformamide (10 ml) was stirred at a bath temperature of 90° to 100° C. for 2 hours. After completion of the reaction, toluene (100 ml) was added to the mixture, which was washed three times with water (50 ml). The toluene layer was washed with a saturated sodium chloride solution and dried over magnesium sulfate. The crude oil thus obtained was purified by silica gel chromatography to give the objective compound. IR νmaxNujol (cm-1): 1590, 1560, 1490, 1450, 1420.

Workup

  1. additionwas added to the mixture, which
  2. washwas washed three times with water (50 ml)
  3. washThe toluene layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe crude oil thus obtained
  6. customwas purified by silica gel chromatography
  7. customto give the objective compound

Sources & evidence

ORD record
ord-01bbabe873304fbfb3213f7399eebd9f
Source dataset
uspto-grants-1988_05
Patent number
US04745117

Reaction notes

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