Dicyclohexylcarbodiimide → HCID 178444548, compound

HRID 1086971Notes

Reaction equation

HRID 1086971 reaction equation
[CH3:1][CH:2]([C:5]1[S:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[N:8][N:9]=1)[CH2:3][CH3:4].[CH2:17]([C@H:22]1[CH2:27][CH2:26][C@H:25]([C:28](O)=[O:29])[CH2:24][CH2:23]1)[CH2:18][CH2:19][CH2:20][CH3:21].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CN=2)CCCC1>C(Cl)Cl>[CH3:1][CH:2]([C:5]1[S:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([O:16][C:28]([C@H:25]3[CH2:26][CH2:27][C@H:22]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:23][CH2:24]3)=[O:29])=[CH:14][CH:15]=2)=[N:8][N:9]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218558524-(1-Pyrrolidinyl)pyrimidineHCID 1357784881-Methylpropyl-5-[4-hydroxyphenyl]-1,3,4-thiadiazoleHCID 178444557HCID 178444557, compound

Product 1

HCID 178444548HCID 178444548, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a mixture of 0.3 g (1.28×10-3 mol) of 1-methylpropyl-5-[4-hydroxyphenyl]-1,3,4-thiadiazole, 0.26 g (1.31×10-3 mol) of trans-4-n-pentylcyclohexanecarboxylic acid, 0.27 g (1.31×10-3 mol) of dicyclohexylcarbodiimide and 0.03 g of 4-(1-pyrrolidinyl)pyrimidine, 15 ml of methylene chloride was added, followed by 20 hours of stirring at room temperature. After the reaction, the reaction was filtered and the solid was washed with methylene chloride. The filtrate and the washing liquid were dehydrated, and the solvent was distilled off therefrom to obtain a crude product, which was then recrystallized twice to obtain 0.24 g of 2-(1-methylpropyl)-5-[4-(trans-4-n-pentylcyclohexylcarbonyloxy)-phenyl]-1,3,4-thiadiazole. (Yield: 45.2%).

Workup

  1. additionwas added
  2. customAfter the reaction
  3. filtrationthe reaction was filtered
  4. washthe solid was washed with methylene chloride
  5. distillationthe solvent was distilled off
  6. customto obtain a crude product, which
  7. customwas then recrystallized twice

Sources & evidence

ORD record
ord-1f6ca3367e6c4a789589b764dd7ea3f3
Source dataset
uspto-grants-1991_07
Patent number
US05034151

Reaction notes

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