1-Bromohexadecane → HCID 20396838, compound

HRID 1112477Notes

Reaction equation

HRID 1112477 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-874873ea19f4420c94f6587ed7c88504
Source dataset
uspto-grants-1978_10
Patent number
US04122272

Reaction notes

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