Acetic Acid → HCID 178446445, compound

HRID 358815Notes

Reaction equation

HRID 358815 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][CH3:5].C(O)(=O)C.[C:11]([NH:14][C:15]([NH2:17])=[S:16])(=N)[NH2:12]>C(O)C>[CH2:1]([NH:6][C:11]([NH:14][C:15]([NH2:17])=[S:16])=[NH:12])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8060PentylamineHCID 178513045HCID 178513045, compound

Product 1

HCID 178446445HCID 178446445, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a one liter, 3-necked round bottom flask which was equipped with a mechanical stirrer, thermometer, and reflux condenser were added absolute ethanol (180 ml.) and pentylamine (100.0 g., 1.15 mol). The amine solution was cooled in an ice bath while glacial acetic acid (68.9 g., 1.15 mol) was slowly added. Amidinothiourea (90.37 g., 0.76 mol) was added and then the mixture was heated to reflux (85° C.). After 24 hours at reflux, HPLC analysis of the reaction solution indicated that title product (72.6 area %) had formed and that residual amidinothiourea (8.5 area %) remained.

Workup

  1. customTo a one liter, 3-necked round bottom flask which was equipped with a mechanical stirrer
  2. temperaturethermometer, and reflux condenser
  3. additionwas slowly added
  4. temperaturethe mixture was heated
  5. temperatureAfter 24 hours at reflux

Sources & evidence

ORD record
ord-78ed4cbd7a3a4443a9fc9c21be532034
Source dataset
uspto-grants-1991_03
Patent number
US04997949

Reaction notes

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