3,5-Difluorophenylacetic acid → HCID 86662121, compound

HRID 1035742Notes

Reaction equation

HRID 1035742 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:13][NH:14][C:15]([NH2:17])=[S:16].OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:14]([C:15](=[S:16])[NH2:17])[NH2:13])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 1454243,5-Difluorophenylacetic acidHCID 2723789ThiosemicarbazideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 86662121HCID 86662121, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.5 g of 3,5-difluorophenylacetic acid (14.52 mmol, 1 eq.) are placed in 70 mL of dichloromethane with stirring. 1.46 g of thiosemicarbazide (15.98 mmol, 1.1 eq.), 2.22 g of hydroxybenzotriazole (14.52 mmol, 1 eq.) and 2.78 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (14.52 mmol, 1 eq.) are successively added with continued stirring at room temperature. After 18 hours at room temperature, the dichloromethane is evaporated off. The residue is taken up in ethyl acetate and 1N hydrochloric acid. The precipitate is filtered off and dried to give 1.67 g of [(3,5-difluorophenyl)acetyl]hydrazinecarbothioamide.

Workup

  1. stirringwith continued stirring at room temperature
  2. customthe dichloromethane is evaporated off
  3. filtrationThe precipitate is filtered off
  4. customdried

Sources & evidence

ORD record
ord-6e3fb33811ae474493a04d01990f39cc
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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