Dicyclohexylcarbodiimide → HCID 18997772, compound

HRID 2260469Notes

Reaction equation

HRID 2260469 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([C:23]1[S:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)=[N:26][N:27]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH3:35][C:36]([C:44]#[N:45])([CH2:40][CH2:41][CH2:42][CH3:43])[C:37](O)=[O:38]>ClCCl>[C:44]([C:36]([CH3:35])([CH2:40][CH2:41][CH2:42][CH3:43])[C:37]([O:34][C:31]1[CH:30]=[CH:29][C:28]([C:25]2[S:24][C:23]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[N:27][N:26]=2)=[CH:33][CH:32]=1)=[O:38])#[N:45]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14495733HCID 14495733, compoundHCID 135710781HCID 135710781, compound

Product 1

HCID 18997772HCID 18997772, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

With exclusion of moisture, 0.1 mol of dicyclohexylcarbodiimide in dichloromethane is added to a mixture of 0.1 mol of 2-heptyl-5-p-hydroxyphenyl-1,3,4-thiadiazole and 0.1 mol of optically active 2-methyl-2-butylcyanoacetic acid in 200 mL of dichloromethane, while cooling with ice. The mixture is stirred for a further 12 hours at room temperature, the dicyclohexyl urea is filtered off and 2-[4-(2-cyano-2-methylhexanoyloxy)-phenyl]-5-n-heptyl-1,3,4-thiadiazole is isolated by working up in the usual way.

Workup

  1. temperaturewhile cooling with ice
  2. filtrationthe dicyclohexyl urea is filtered off

Sources & evidence

ORD record
ord-32a6635e788843f19316e95ed6a537ce
Source dataset
uspto-grants-1995_12
Patent number
US05478496

Reaction notes

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