Dicyclohexylcarbodiimide → HCID 14344654, compound

HRID 2291977Notes

Reaction equation

HRID 2291977 reaction equation
[C:1]([CH2:4][N:5]1[C:9](=[O:10])[CH2:8][S:7][C:6]1=[S:11])([OH:3])=O.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH:20][CH:21]=[O:22])=[CH:15][CH:14]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH:21]([NH:20][NH:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:1]([CH2:4][N:5]2[C:9](=[O:10])[CH2:8][S:7][C:6]2=[S:11])=[O:3])=[CH:14][CH:15]=1)=[O:22]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-

Product 1

HCID 14344654HCID 14344654, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1.91 g (10 millimole) of 3-carboxymethylrhodanine, 1.51 g (10 millimole) of 2-(4-aminophenyl)-1-formylhydrazine and 2.06 g (10 millimole) of N,N'-dicyclohexylcarbodiimide was added 50 ml of tetrahydrofuran. The resulting mixture was stirred for 5 hours at room temperature to precipitate crystals. These were filtered off, and dissolved in 50 ml of N,N-dimethylformamide (DMF). The matter remaining insoluble was removed from the solution. 100 ml of water was added to the filtrate, and allowed to stand for one night to precipitate crystals. These were filtered off, and washed with water and methanol. Thus, the intended compound was obtained. Yield, 2.98 g (92%). Melting Point, 260° C. (decomposed).

Workup

  1. customto precipitate crystals
  2. filtrationThese were filtered off
  3. dissolutiondissolved in 50 ml of N,N-dimethylformamide (DMF)
  4. customThe matter remaining insoluble was removed from the solution
  5. addition100 ml of water was added to the filtrate
  6. waitto stand for one night
  7. customto precipitate crystals
  8. filtrationThese were filtered off
  9. washwashed with water and methanol
  10. customThus, the intended compound was obtained
  11. customYield

Sources & evidence

ORD record
ord-ca70ec6f852648758b6051522e1d2274
Source dataset
uspto-grants-1989_01
Patent number
US04800154

Reaction notes

Loading…