1-Bromohexadecane → HCID 20396833, compound

HRID 616892Notes

Reaction equation

HRID 616892 reaction equation
[CH2:1]([C:3]1[N:7]2[CH2:8][CH2:9][CH2:10][N:11]=[C:6]2[S:5][C:4]=1[CH3:12])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH2:19]([Br:35])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>C(#N)C>[Br-:35].[CH2:34]([N:11]1[CH2:10][CH2:9][CH2:8][N+:7]2[C:3]([CH2:1][CH3:2])=[C:4]([CH3:12])[S:5][C:6]1=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19]

Participants

5

Reactant 3

HCID 82131-BromohexadecaneHCID 10340Sodium CarbonateHCID 203968403-Ethyl-2-methyl-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine

Product 1

HCID 20396833HCID 20396833, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

3-Ethyl-2-methyl-6,7-dihydro-[5H]-thiazolo[3,2-a]pyrimidine (1.8 g., 0.01 mole) (prepared by basification of the hydrobromide salt with sodium carbonate) and cetyl bromide (3.3 g., 0.011 mole) were refluxed in acetonitrile solution for 16 hours. The solvent was evaporated and the residual oil solidified by stirring under dry ether at 0° C. Recrystallization from a mixture of acetonitrile and ether gave 8-cetyl-3-ethyl-2-methyl-6,7-dihydro[5H]thiazolo[3,2-a]pyrimidinium bromide, (0.92 g., 20%), m.p. 63°-66° (Found: C, 61.4; H, 9.6; N, 5.6. C25H47N2SBr requires C, 61.6; H, 9.7; N, 5.7%).

Workup

  1. customThe solvent was evaporated
  2. customRecrystallization
  3. additionfrom a mixture of acetonitrile and ether

Sources & evidence

ORD record
ord-59c589593d914c2495d23e1d3fedf364
Source dataset
uspto-grants-1978_02
Patent number
US04076817

Reaction notes

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