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Dicyclohexylcarbodiimide → N-nonadecyl-2-(3-pyridyl)thiazolidine-4-carboxamide

HRID 704429
Notes
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Reaction equation

HRID 704429 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]2[NH:26][CH:25]([C:27]([OH:29])=O)[CH2:24][S:23]2)[CH:17]=1.ON1C2C=CC=CC=2N=N1.[CH2:40]([NH2:59])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]>O1CCCC1.C(OCC)(=O)C>[CH2:40]([NH:59][C:27]([CH:25]1[CH2:24][S:23][CH:22]([C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)[NH:26]1)=[O:29])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1064161-AminononadecaneHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acid

Product 1

HCID 14881554N-nonadecyl-2-(3-pyridyl)thiazolidine-4-carboxamideYield 21.9%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 500 mg of dicyclohexylcarbodiimide in 3 ml of tetrahydrofuran was added dropwise to a mixture of 510 mg of 2-(3-pyridyl)thiazolidine-4-carboxylic acid, 490 mg of 1-hydroxybenzotriazole, 680 mg of nonadecylamine and 12 ml of tetrahydrofuran with ice cooling, and the resulting mixture was stirred with ice cooling for 1 hour and then at room temperature for 12 hours. The reaction mixture was diluted with 30 ml of ethyl acetate, and the insoluble matter was filtered off. The filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) and recrystallized from ethyl acetate to give 250 mg of N-nonadecyl-2-(3-pyridyl)thiazolidine-4-carboxamide. Melting point 108°-110° C.

Workup

  1. waitat room temperature for 12 hours
  2. filtrationthe insoluble matter was filtered off
  3. washThe filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b33b29cc6a4b49c7b2dfc0cdad0ca94c
Source dataset
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04987132

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes