Hydrochloric Acid → HCID 21199940, compound

HRID 1066375Notes

Reaction equation

HRID 1066375 reaction equation
[NH2:1][C:2]1[C:6]([NH2:7])=[CH:5][S:4][CH:3]=1.[C:8](Cl)(=[O:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].Cl>N1C=CC=CC=1>[C:8]([NH:1][C:2]1[C:6]([NH:7][C:8](=[O:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][S:4][CH:3]=1)(=[O:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66982Decanoyl chlorideHCID 643216Thiophene-3,4-diamine

Product 1

HCID 21199940HCID 21199940, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4-Diaminothiophene (2.0 g, 17 mmol) was dissolved in pyridine and the solution was added dropwise to a stirred solution of 6.5 g (34 mmol) of decanoyl chloride (boiling point 125° C. at 45 mbar) via a syringe. It was stirred overnight. The reaction mixture was poured into ice water mixed with concentrated hydrochloric acid and extracted with chloroform. The organic layers were washed with water, 2% strength NaOH and again with water and then dried over MgSO4 which was mixed with active carbon to remove the colored impurities. After evaporating the solvent, a solid was obtained which was recrystallized from a toluene-hexane mixture. The solid had a melting point of 99-100° C. The yield was 6.7 g (90% of theory).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layers were washed with water, 2% strength NaOH and again with water
  3. dry with materialdried over MgSO4 which
  4. additionwas mixed with active carbon
  5. customto remove the colored impurities
  6. customAfter evaporating the solvent
  7. customa solid was obtained which
  8. customwas recrystallized from a toluene-hexane mixture

Sources & evidence

ORD record
ord-445431a3e1b04a32b0264bb7d369da7c
Source dataset
uspto-grants-2001_06
Patent number
US06242561B1

Reaction notes

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