2-Butynedioic acid → [3-Undecyl-2-(undecylimino)-4-oxo-5-thiazolidinylidene]acetic acid

HRID 867441Notes

Reaction equation

HRID 867441 reaction equation
[C:1]([C:6]([OH:8])=[O:7])#[C:2][C:3](O)=[O:4].[CH2:9]([NH:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[S:22])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CO.O1CCCC1>[CH2:24]([N:23]1[C:3](=[O:4])[C:2](=[CH:1][C:6]([OH:8])=[O:7])[S:22][C:21]1=[N:20][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 2

HCID 3712-Butynedioic acidHCID 14390155N,N'-diundecylthiourea

Product 1

HCID 53939534[3-Undecyl-2-(undecylimino)-4-oxo-5-thiazolidinylidene]acetic acidYield 81.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetylenedicarboxylic acid (4.8 g, 40 mmoles) is added to a warm solution of N,N'-diundecylthiourea (15.0 g, 39 mmoles) in methanol (200 mls) and tetrahydrofuran (100 mls). The mixture is stirred for 16 hours at ambient temperature, then concentrated under reduced pressure and cooled. The precipitate is filtered off, rinsed with cold methanol and dried. Recrystallization from methanol afforded the product (15.3 g), mp 67°-68° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. temperaturecooled
  3. filtrationThe precipitate is filtered off
  4. washrinsed with cold methanol
  5. customdried
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-56716c122a934d30a75129b3d2c8b0bb
Source dataset
uspto-grants-1988_10
Patent number
US04775677

Reaction notes

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