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

HRID 863364
Notes
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Reaction equation

HRID 863364 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6342
Acetonitrile
Solvent

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 (1x 50 mL) and the combined ethyl acetate layers were washed with 50 mL water and NaCl solution (2x 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 tide 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 (1x 50 mL)
  6. washthe combined ethyl acetate layers were washed with 50 mL water and NaCl solution (2x 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-6658e9eda7924bfd945ec6c1edb244ed
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05720934

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes