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Sodium Iodide → HCID 14727034, compound

HRID 329418
Notes
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Reaction equation

HRID 329418 reaction equation
Br.[CH3:2][C:3]1[S:4][CH:5]=[CH:6][N:7]=1.[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[N:9]1.C(N([CH:29]([CH3:31])[CH3:30])CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(Cl)Cl.CC(CC(C)C)=O>[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([N:17]2[CH2:18][CH2:19][N:20]([CH2:13][CH2:14][CH2:15][CH2:16][C:30]3[CH:29]=[CH:31][C:12]([C:6]4[N:7]=[C:3]([CH3:2])[S:4][CH:5]=4)=[CH:11][CH:10]=3)[CH2:21][CH2:22]2)=[N:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 86743643HCID 86743643, compound

Product 1

HCID 14727034HCID 14727034, compound

Reagents, catalysts & solvents

2
HCID 6344DichloromethaneSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 100 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.43 g (4.11 mmol) 4-(4-chlorobutyl)phenyl)-2-methylthiazole hydrobromide, 0.90 g. (4.11 mmol) N-benzisothiazolylpiperazine, 0.72 g (4.11 mmol) diisopropylethyl amine, 0.87 g (8.22 mmol) sodium carbonate, 2 mg sodium iodide, and 40 ml methylisobutyl ketone. The reaction was refluxed 31 hours, cooled, filtered, and the filtrate evaporated. The residue was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent to afford an oil, which was taken up in methylene chloride and precipitated by addition of ether saturated with HCl. The solid was filtered, washed with ether, dried briefly, then washed with a minimal amount of acetone and dried to afford a white solid, m.p. 207-212° C., 1.87 g (87.2%). NMR (DMSO-d6): 1.6-1.8 (m, 4H), 2.64 (t, 2H), 2.72 (s, 3H), 3.1-3.3 (m, 4H), 3.4-3.6 (m,4 H), 4.0 (d, 2H), 7.2-8.1 (m, 8H), 7.85 (s, 1H).

Workup

  1. customTo a 100 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 31 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customThe residue was chromatographed on silica gel
  7. customto afford an oil, which
  8. customprecipitated by addition of ether saturated with HCl
  9. filtrationThe solid was filtered
  10. washwashed with ether
  11. customdried briefly
  12. washwashed with a minimal amount of acetone
  13. customdried
  14. customto afford a white solid, m.p. 207-212° C., 1.87 g (87.2%)

Sources & evidence

ORD record
ord-ac41fa10cf124ce8b5ea981e51e856f6
Source dataset
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04891375

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes