Potassium Carbonate → HCID 18764640, compound

HRID 1251634Notes

Reaction equation

HRID 1251634 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH2:6]([NH2:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.O>[Br:1][CH2:2][C:3]([NH:24][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15793OctadecylamineHCID 61147Bromoacetyl bromide

Product 1

HCID 18764640HCID 18764640, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromoacetyl bromide (44.4 g; 0.22 mol) in CH2Cl2 (50 mL) was added dropwise in 2.5 h at 20° C. to a mixture of octadecylamine (59.3 g; 0.22 mol) and K2CO3 (30.4 g; 0.22 mol) in CH2Cl2 (600 mL) and H2O (600 mL). After 16 h at room temperature the organic layer was separated, washed with H2O, dried over Na2SO4 and evaporated. The crude product was purified by flash chromatography (CH2Cl2/MeOH=100/1 (v/v)) to give the desired product (60 g; 0.154 mol). Yield 70%. GC: 96% (area %), K. F.: <0.1%; 1H-NMR, 13C-NMR and MS spectra were consistent with the postulated structure.

Workup

  1. customAfter 16 h at room temperature the organic layer was separated
  2. washwashed with H2O
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe crude product was purified by flash chromatography (CH2Cl2/MeOH=100/1 (v/v))

Sources & evidence

ORD record
ord-206fc276e600414fb3cd831fdeafd258
Source dataset
uspto-grants-2002_01
Patent number
US06342598B1

Reaction notes

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