Thionyl Chloride → HCID 21443926, compound

HRID 328110Notes

Reaction equation

HRID 328110 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].S(Cl)([Cl:16])=O>C1C=CC=CC=1.CN(C)C=O>[ClH:16].[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([Cl:16])=[O:13])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 103133572-(4-carbamimidoylphenyl)acetic Acid

Product 1

HCID 21443926HCID 21443926, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

5.35 g of 4-amidinophenylacetic acid (M.p. 295° to 297° C, decomposition) were suspended in 45 ml of anhydrous benzene. Two drops of dimethylformamide and 17.9 g of thionyl chloride were added and the whole was heated for 11/2 hours under reflux. After cooling, the solid product was filtered off with suction, washed with anhydrous benzene and dried under reduced pressure. 6.9 g of 4-amidino-phenylacetyl chloride-hydrochloride melting at 174° to 177° C (decomposition) were obtained.

Workup

  1. temperaturethe whole was heated for 11/2 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationthe solid product was filtered off with suction
  5. washwashed with anhydrous benzene
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-d93d65c20ae7453291def8277cf8f509
Source dataset
uspto-grants-1977_04
Patent number
US04016159

Reaction notes

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