Sodium Iodide → HCID 14580036, compound

HRID 1087484Notes

Reaction equation

HRID 1087484 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(N(CC)CC)C.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1.[I-].[Na+]>C1(C)C=CC=CC=1>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([N:33]2[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][CH2:4][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]5[CH:14]=[CH:15][CH:16]=[C:7]([C:8]=45)[S:6]3(=[O:18])=[O:17])[CH2:35][CH2:34]2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 974781-(4-Chlorophenyl)piperazineHCID 145800262(3-Chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide

Product 1

HCID 14580036HCID 14580036, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 (5.3 g), triethylamine (2.6 cc), 4-(4-chlorophenyl) piperazine (5 g) and sodium iodide (2.8 g) in toluene (50 cc). The mixture is heated for 6 hours at boiling point, then cooled to a temperature of about 20° C. After recrystallization, firstly from boiling acetonitrile 6 hours and secondly from boiling methyl ethyl ketone (15 cc), 2-{3-[4-(4-chlorophenyl)-1-piperazinyl ]propyl}naptho[1,8-cd]isothiazole 1,1-dioxide (3 g) is obtained, m.p. 120° C.

Workup

  1. temperatureThe mixture is heated for 6 hours
  2. customAfter recrystallization
  3. customacetonitrile 6 hours

Sources & evidence

ORD record
ord-4b40a5315820467f8a71aa51acbe6f20
Source dataset
uspto-grants-1991_07
Patent number
US05036075

Reaction notes

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