Chloride → HCID 86744100, compound

HRID 2165752Notes

Reaction equation

HRID 2165752 reaction equation
C[O:2][C:3](=[O:32])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=O)[CH2:10]CCCCCCCCCC/C=C\CCCCCCCC.[C:33]([OH:56])(=O)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]/[CH:45]=[CH:46]\[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54].[Cl-].N1C=CC(C2[NH:68][CH:67](C(O)=O)[CH2:66][S:65]2)=CC=1>N1C=CC=CC=1.C(Cl)Cl>[C:33]([N:68]1[CH:67]=[CH:66][S:65][C:4]1([C:8]1[CH:7]=[CH:6][N:5]=[CH:9][CH:10]=1)[C:3]([OH:2])=[O:32])(=[O:56])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]/[CH:45]=[CH:46]\[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]

Participants

7

Reactant 4

HCID 312ChlorideHCID 999852-(Pyridin-4-yl)-1,3-thiazolidine-4-carboxylic acidHCID 5281116Erucic AcidHCID 70363053HCID 70363053, compound

Product 1

HCID 86744100HCID 86744100, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

In a manner similar to (i), erucic acid (1 g) was converted to its chloride, to which was added 2-(4-pyridinyl)-4-thiazolidine carboxylic acid (618 mg). The mixture was stirred in pyridine (6 ml)-methylene chloride (2 ml) at room temperature for two hours. The solvent was concentrated, then the residue was washed with water. Resultant precipitates were dried and purified by means of a silica gel column chromatography (chloroform:methanol=10:1), followed by recrystallization from methanol to afford colorless crystals [1.58 g (yield 99%)], m.p. 156 to 158° C.

Workup

  1. concentrationThe solvent was concentrated
  2. washthe residue was washed with water
  3. customResultant precipitates
  4. customwere dried
  5. custompurified by means of a silica gel column chromatography (chloroform:methanol=10:1)
  6. customfollowed by recrystallization from methanol
  7. customto afford colorless crystals [1.58 g (yield 99%)], m.p. 156 to 158° C.

Sources & evidence

ORD record
ord-134d1966baa54bd696e76c9e1e89256a
Source dataset
uspto-grants-1990_07
Patent number
US04940730

Reaction notes

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