Cyclopentanecarboxylic acid → HCID 178514279, compound

HRID 1840726Notes

Reaction equation

HRID 1840726 reaction equation
[NH2:1][NH:2][C:3]([NH:5][NH2:6])=[S:4].[CH:7]1([C:12](O)=O)[CH2:11][CH2:10][CH2:9][CH2:8]1>O>[NH2:1][N:2]1[C:12]([CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[N:6][N:5]=[C:3]1[SH:4]

Participants

4

Reactant 2

HCID 18840Cyclopentanecarboxylic acidHCID 2724189Thiocarbohydrazide

Product 1

HCID 178514279HCID 178514279, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

34.29 g (323 mmol) of finely mortared thiocarbohydrazide are suspended in 38.5 ml (355.3 mmol) of cyclopentanecarboxylic acid and the suspension is heated at 165° C. for 20 min. During this, the water produced in the reaction is distilled off until a yellowish condensate appears. After cooling down, 250 ml of dichloromethane/methanol 95:5 are added to the suspension and the precipitate is filtered off. The filtrate is concentrated and subject to column filtration on silica gel (dichloromethane/methanol 98:2). After drying under high vacuum, the product is obtained as a colorless solid.

Workup

  1. distillationis distilled off until a yellowish condensate
  2. temperatureAfter cooling down
  3. addition250 ml of dichloromethane/methanol 95:5 are added to the suspension
  4. filtrationthe precipitate is filtered off
  5. concentrationThe filtrate is concentrated
  6. filtrationsubject to column filtration on silica gel (dichloromethane/methanol 98:2)
  7. customAfter drying under high vacuum
  8. customthe product is obtained as a colorless solid

Sources & evidence

ORD record
ord-454d0e901f1445aba22e38859091d5e2
Source dataset
uspto-grants-2004_01
Patent number
US06683081B2

Reaction notes

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