Potassium Carbonate → N-(5-carboethoxypentyl)-N,N'-bis(2-methyl-2-triphenylmethylthiopropyl)ethylenediamine

HRID 1955474Notes

Reaction equation

HRID 1955474 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].[CH3:7][C:8]([S:39][C:40]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([CH3:38])[CH2:9][NH:10][CH2:11][CH2:12][NH:13][CH2:14][C:15]([S:18][C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:17])[CH3:16].Br[CH2:60][CH2:61][CH2:62][CH2:63][C:64]([O:66][CH2:67][CH3:68])=[O:65]>CC#N>[C:64]([CH2:63][CH2:62][CH2:61][CH2:60][CH2:1][N:10]([CH2:9][C:8]([CH3:7])([S:39][C:40]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)([C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH3:38])[CH2:11][CH2:12][NH:13][CH2:14][C:15]([S:18][C:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([CH3:16])[CH3:17])([O:66][CH2:67][CH3:68])=[O:65]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 21192173N,N'-bis(2-methyl-2-triphenylmethylthiopropyl)ethylenediamine

Product 1

HCID 18702528N-(5-carboethoxypentyl)-N,N'-bis(2-methyl-2-triphenylmethylthiopropyl)ethylenediamineYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

K2CO3 (1.92 g, 13.9 mmol, 100 mol %) was added to N,N'-bis(2-methyl-2-triphenylmethylthiopropyl)ethylenediamine (10.03 g, 13.9 mmol) in CH3CN (60 mL), followed by ethyl 5-bromovalerate (3.30 mL, 20.8 mmol, 150 mol %). The reaction was heated at reflux under argon overnight. The solution was then concentrated to a paste and partitioned between 0.25M KOH (100 mL)and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (1×50 mL) and the combined ethyl acetate layers were washed with 50 mL water and NaCl solution (2×50 mL), dried with Na2SO4 and concentrated to an orange oil. Purification by flash chromatography (300 g flash silica, 100% CHCl3 to 5% MeOH/CHCl3) gave pure title compound (7.75 g, 66% yield). FABMS analysis yielded an (MH+) of 849 (compared with a calculated molecular weight of 849.24 for the compound C55H64N2O2 S2).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux under argon overnight
  3. concentrationThe solution was then concentrated to a paste
  4. custompartitioned between 0.25M KOH (100 mL)and ethyl acetate (100 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (1×50 mL)
  6. washthe combined ethyl acetate layers were washed with 50 mL water and NaCl solution (2×50 mL)
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated to an orange oil
  9. customPurification by flash chromatography (300 g flash silica, 100% CHCl3 to 5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-4b88b28234914a28988fd5a1e008f5a8
Source dataset
uspto-grants-1998_07
Patent number
US05776428

Reaction notes

Loading…