Sodium Bicarbonate → HCID 15646683, compound

HRID 1087516Notes

Reaction equation

HRID 1087516 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=23)[S:6]1(=[O:18])=[O:17].C(=O)(O)[O-].[Na+].[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]=[C:28]2[C:34]1[CH2:35][CH2:36][NH:37][CH2:38][CH:39]=1>CN(C)C=O.O1CCCC1>[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]=[C:28]2[C:34]1[CH2:35][CH2:36][N:37]([CH2:2][CH2:3][CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=34)[S:6]2(=[O:18])=[O:17])[CH2:38][CH:39]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 145800262(3-Chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide

Product 1

HCID 15646683HCID 15646683, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

The experiment is carried out as in Example 1, starting with 2-(3-chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (2.4 g), sodium bicarbonate (0.7 g) and 4-(5-chloro-3-indolyl)-1,2,3,6-tetrahydropyridine (2 g) in dimethylformamide (15 cc) and tetrahydrofuran (15 cc). The mixture is heated for 5 hours at boiling point, then cooled to a temperature of about 20° C. Stirring is maintained for 7 hours at this temperature. After purification by crystallization from water (50 cc), then recrystallization from boiling acetonitrile (50 cc), 2-{3-[4-(5-chloro-3-indolyl)-1,2,3,6-tetrahydro-1-pyridyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (2.1 g) is obtained, m.p. 189° C.

Workup

  1. temperatureThe mixture is heated for 5 hours
  2. temperatureis maintained for 7 hours at this temperature
  3. customAfter purification
  4. customby crystallization from water (50 cc)
  5. customrecrystallization

Sources & evidence

ORD record
ord-6e30354a990843758138e3f7ceb93880
Source dataset
uspto-grants-1991_07
Patent number
US05036075

Reaction notes

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