Cesium carbonate → HCID 86755581, compound

HRID 1870604Notes

Reaction equation

HRID 1870604 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:5]1=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+].[H-].[Na+].[O:30]=[S:31]1(=[O:47])[C:35]2[CH:36]=[CH:37][C:38]([Cl:40])=[CH:39][C:34]=2[C:33](=O)[N:32]1[CH2:42][CH2:43][CH2:44][CH2:45]Br>>[O:47]=[S:31]1(=[O:30])[C:35]2[CH:36]=[CH:37][C:38]([Cl:40])=[CH:39][C:34]=2[CH2:33][N:32]1[CH2:42][CH2:43][CH2:44][CH2:45][N:16]1[CH2:15][CH2:14][CH:13]([N:6]2[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:4]([CH2:3][C:2]([F:1])([F:20])[F:21])[C:5]2=[O:19])[CH2:18][CH2:17]1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 24758Sodium hydrideHCID 133659801,2-Benzisothiazol-3(2H)-one, 2-(4-bromobutyl)-5-chloro-, 1,1-dioxideHCID 186959501,3-Dihydro-1-(4-piperidinyl)-3-(2,2,2-trifluoroethyl)-2H-benzimidazol-2-one

Product 1

HCID 86755581HCID 86755581, compound

Procedure

From 4-(3-(2,2,2-trifluoroethyl)-2-oxo-1-benzimidazolinyl)piperidine [prepared by a modification of Step 2 of Example 1 wherein cesium carbonate replaced the sodium hydride and the reaction was heated at 50° C. for 20 hours] and 1,1-dioxido-2-(4-bromobutyl)-5-chloro-1,2-benzisothiazol-3(2H)-one using the procedures described in Example 1 there was obtained a white solid upon formation of the HCl salt (from methanol and diethyl ether), melting point 237-239° C. Analysis calculated for C25H26ClF3N4O4S.HCl.0.4 H2O: C,48.85; H,4.56; N,9.12; found: C,48.83 ; H,4.53 ; N,9.04. The NMR was consistent with the structure.

Sources & evidence

ORD record
ord-feaa11dce13d4084b01961c8ed636ab9
Source dataset
uspto-grants-2000_08
Patent number
US06096763

Reaction notes

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