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Dimethylamine → Sodium 5-(3-(7-chloroquinolin-2-ylmethylthio)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

HRID 232418
Notes
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Reaction equation

HRID 232418 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][S:13][C:14]3[CH:15]=[C:16]([CH:20]([S:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[S:21][CH2:22][CH2:23][C:24](O)=[O:25])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[I-].Cl[C:35]1C=CC=[CH:37][N+:36]=1C.CNC.[OH-].[Na+:46]>ClCCl.C(#N)C.C1(C)C=CC=CC=1.C(O)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][S:13][C:14]3[CH:15]=[C:16]([CH:20]([S:21][CH2:22][CH2:23][C:24](=[O:25])[N:36]([CH3:37])[CH3:35])[S:27][CH2:28][CH2:29][C:30]([O-:32])=[O:31])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[Na+:46]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 1670692-Chloro-1-methylpyridinium iodideHCID 104139205-(3-(7-Chloroquinolin-2-ylmethylthio)phenyl)-4,6-dithianonanedioic acid

Product 1

HCID 23683603Sodium 5-(3-(7-chloroquinolin-2-ylmethylthio)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of diacid (Step 4) (360 mg) in dichloromethane (28 mL) and acetonitrile (7.1 mL) was added 2-chloro-1-methylpyridinium iodide (227 mg). The solution was cooled to 0 C. and triethylamine (123 μL) was added. After stirring for 15 min, 0.42 mL of a 2M solution of dimethylamine in toluene was added. The solution was stirred 1 hr at room temperature, washed with acidified 25% ammonium acetate, dried over sodium sulfate, filtered and evaporated to dryness. To the oil obtained after chromatography, in 2 mL of ethanol, was added 0.154 mL of 2N NaOH. After evaporating to dryness the title compound was obtained as a foam.

Workup

  1. temperatureThe solution was cooled to 0 C
  2. stirringThe solution was stirred 1 hr at room temperature
  3. washwashed
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customTo the oil obtained after chromatography
  8. customAfter evaporating to dryness the title compound
  9. customwas obtained as a foam

Sources & evidence

ORD record
ord-5f7a9d445a1041dabcc8883dae5be96b
Source dataset
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04851409

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes