1-Bromohexadecane → HCID 20396838, compound

HRID 616893Notes

Reaction equation

HRID 616893 reaction equation
[CH3:1][C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][N:11]=[C:5]2[S:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:18]([Br:34])[CH2:19][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][CH3:33]>C(#N)C>[Br-:34].[CH2:33]([N:11]1[CH2:10][CH2:9][CH2:8][CH2:7][N+:6]2[C:2]([CH3:1])=[CH:3][S:4][C:5]1=2)[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][CH2:19][CH3:18]

Participants

5

Reactant 3

HCID 82131-BromohexadecaneHCID 10340Sodium CarbonateHCID 4318663-Methyl-5,6,7,8-tetrahydro(1,3)thiazolo(3,2-a)(1,3)diazepine

Product 1

HCID 20396838HCID 20396838, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3-Methyl-5,6,7,8-tetrahydro-thiazolo[3,2-a][1,3]diazepine (1.68 g., 0.01 mole) (prepared by basification of the hydrochloride salt with sodium carbonate in acetonitrile solution) was dissolved in dry acetonitrile and refluxed for 36 hours with cetyl bromide (3.4 g., 0.011 mole). The solvent was evaporated and the residue washed with toluene and dried. Recrystallization from a mixture of acetonitrile and dry ether gave 9-cetyl-3-methyl-5,6,7,8-tetrahydro-thiazolo[3,2-a][1,3]diazepinium bromide (3.9 g., 81%) m.p. 120°-121°. (Found: C, 60.5; H, 9.5; N, 6.2. C24H45N2SBr requires C, 60.8; H, 9.5; N, 5.9%).

Workup

  1. customThe solvent was evaporated
  2. washthe residue washed with toluene
  3. customdried
  4. customRecrystallization
  5. additionfrom a mixture of acetonitrile and dry ether

Sources & evidence

ORD record
ord-663c136d51e54536b60cbb8773a43464
Source dataset
uspto-grants-1978_02
Patent number
US04076817

Reaction notes

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