Benzoyl chloride → HCID 86744951, compound

HRID 1087517Notes

Reaction equation

HRID 1087517 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[C:24]5[CH:25]=[CH:26][CH:27]=[C:18]([C:19]=45)[S:17]3(=[O:29])=[O:28])[CH2:9][CH2:8]2)[C:5]2[CH:30]=[CH:31][CH:32]=[CH:33][C:4]=2[NH:3]1.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[H-].[Na+]>CN(C)C=O.O1CCCC1>[C:34]([N:3]1[C:4]2[CH:33]=[CH:32][CH:31]=[CH:30][C:5]=2[N:6]([CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[C:24]5[CH:25]=[CH:26][CH:27]=[C:18]([C:19]=45)[S:17]3(=[O:29])=[O:28])[CH2:11][CH2:12]2)[C:2]1=[O:1])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 157107272-{3-[4-(2-Oxo-1-benzimidazolinyl)piperidino]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide

Product 1

HCID 86744951HCID 86744951, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

The experiment is carried out as in Example 44, starting with 2-{3-[4-(2-oxo-1-benzimidazolinyl)piperidino]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (4.6 g) in dimethylformamide (20 cc) and benzoyl chloride (1.4 g) in tetrahydrofuran (20 cc) and sodium hydride (0.48 g) as a 50% dispersion in vaseline oil. The mixture is stirred for 15 hours at a temperature of about 20° C. After purification by flash-chromatography on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with a dichloromethanemethanol (90-10 vol) mixture as eluant, and then recrystallization from a boiling acetone/ethanol (90-10 vol) mixture (60 cc), 2-{3-[4-(3-benzoyl-2-oxo-1-benzimidazolinyl)piperidino]propyl}naphto [1,8-cd]isothiazole 1,1-dioxide (2.9 g) is obtained, m.p. 133° C.

Workup

  1. customAfter purification by flash-chromatography on a silica column
  2. customunder a current of argon at medium pressure (0.5-1.5 bar) with a dichloromethanemethanol (90-10 vol) mixture as eluant, and then recrystallization from a boiling acetone/ethanol (90-10 vol) mixture (60 cc)

Sources & evidence

ORD record
ord-c4daeb6dfb814ac9812a0d8ebc413f50
Source dataset
uspto-grants-1991_07
Patent number
US05036075

Reaction notes

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