2-(4-Fluorophenyl)acetic acid → 2-[(4-Fluorophenyl)acetyl]hydrazinecarbothioamide

HRID 1035684Notes

Reaction equation

HRID 1035684 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:12][NH:13][C:14]([NH2:16])=[S:15].OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:12][NH:13][C:14](=[S:15])[NH2:16])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 98372-(4-Fluorophenyl)acetic acidHCID 2723789ThiosemicarbazideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 214972132-[(4-Fluorophenyl)acetyl]hydrazinecarbothioamideYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g of 4-fluorophenylacetic acid (32.44 mmol, 1 eq.) are placed in 50 mL of dichloromethane with stirring. 3.25 g of thiosemicarbazide (35.68 mmol, 1 eq.), 4.38 g of hydroxybenzotriazole (32.44 mmol, 1 eq.) and 6.22 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (32.44 mmol, 1.2 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, washed three times with water, once with brine and three times with 1N hydrochloric acid. The organic phase is dried over sodium sulfate and evaporated to give 5 g of 2-[(4-fluorophenyl)acetyl]hydrazinecarbothioamide. M-isobutene+=228.

Workup

  1. stirringwith continued stirring at room temperature
  2. customthe dichloromethane is evaporated off
  3. washwashed three times with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2d9177aab14e435bab0c8b22c33a5a2e
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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