Dodecanoyl chloride → HCID 10730991, compound

HRID 2081658Notes

Reaction equation

HRID 2081658 reaction equation
[C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:15][NH:16][C:17]([NH2:19])=[S:18]>C1COCC1>[NH2:19][C:17](=[S:18])[NH:16][NH:15][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 8166Dodecanoyl chlorideHCID 2723789Thiosemicarbazide

Product 1

HCID 10730991HCID 10730991, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lauroyl chloride (12.9 g, 0.06 mol) in THF (70 mL) was added dropwise to a vigorously stirred suspension of thiosemicarbazide (10.9 g, 0.12 mol) in THF (300 mL) at 0° C. After the addition was complete, the mixture was allowed to warm to room temperature and stirred for 24 hours. The mixture was concentrated in vacuo to one-quarter of the original volume and filtered through a silica pad, eluting with ethyl acetate (500 mL). The filtrate was concentrated to 250 mL, filtered, and the residue washed with ethyl acetate and dried in vacuo to give 12.0 g of a white solid.

Workup

  1. additionAfter the addition
  2. concentrationThe mixture was concentrated in vacuo to one-quarter of the original volume
  3. filtrationfiltered through a silica pad
  4. washeluting with ethyl acetate (500 mL)
  5. concentrationThe filtrate was concentrated to 250 mL
  6. filtrationfiltered
  7. washthe residue washed with ethyl acetate
  8. customdried in vacuo

Sources & evidence

ORD record
ord-870d85ce7b3b4363ac0e975bb79ef100
Source dataset
uspto-grants-1993_02
Patent number
US05185358

Reaction notes

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