Chloroform → HCID 22764381, compound

HRID 616894Notes

Reaction equation

HRID 616894 reaction equation
[CH3:1][C:2]1[S:6][C:5]2=[N:7][CH2:8][CH2:9][N:4]2[C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)(Cl)Cl.[CH2:26]([Br:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C(#N)C>[Br-:42].[CH2:41]([N:7]1[C:5]2[S:6][C:2]([CH3:1])=[C:3]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[N+:4]=2[CH2:9][CH2:8]1)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH3:26]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 82131-BromohexadecaneHCID 10340Sodium CarbonateHCID 20396841HCID 20396841, compound

Product 1

HCID 22764381HCID 22764381, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methyl-3-phenyl-5,6-dihydro-imidazo[2,1-b]thiazole (6.0 g., 0.027 mole) (prepared by basification of the hydrobromide salt with sodium carbonate solution and extraction into chloroform) and cetyl bromide (9.15 g., 0.03 mole) were refluxed in acetonitrile (50 ml.) for 12 hours. A crystalline solid separated on cooling which was collected and recrystallized from acetonitrile to yield 7-cetyl-2-methyl-3-phenyl-5,6-dihydro-imidazo[2,1-b]thiazolium bromide (12.2 g., 87%), m.p. 111°-113° C. (Found: C, 64.8; H, 8.6; N, 4.9. C28H45N2SBr requires C, 64.5; H, 8.6; N, 5.4%).

Workup

  1. customA crystalline solid separated
  2. temperatureon cooling which
  3. customwas collected
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-fac6555885954f569db86e331f457cbb
Source dataset
uspto-grants-1978_02
Patent number
US04076817

Reaction notes

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