Chloroform → HCID 22764381, compound

HRID 971959Notes

Reaction equation

HRID 971959 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-110a1a6448b74a7bb500df5a60df870d
Source dataset
uspto-grants-1979_07
Patent number
US04162253

Reaction notes

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