Phenylacetic Acid → HCID 86761678, compound

HRID 1876906Notes

Reaction equation

HRID 1876906 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][S:11][C:10]2=[NH:14])=[CH:4][N:3]=1.Cl.C(N=C=NCCCN(C)C)C.[C:27]1([CH2:33][C:34](O)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][S:11][CH:10]2[NH:14][C:34](=[O:35])[CH2:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 999Phenylacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 98593863-[(6-Chloro-3-pyridinyl)methyl]-2-thiazolidinimine

Product 1

HCID 86761678HCID 86761678, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-Chloro-5-pyridinylmethyl)-2-iminothiazolidine (132 mg, 0.5 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (96 mg, 0.5 mmol) and 4-dimethylaminopyridine (65 mg, 0.54 mmol) in 3 ml of dichloromethane, phenylacetic acid (68 mg, 0.5 mmol) was added in portions, and stirred at room temperature overnight. After distilling the solvent off, the resultant crude crystal was washed with 1% hydrochloric acid, recrystallized from ethyl acetate thereby obtaining the intended substance. Yield: 100 mg (58%). Melting point: 157-158° C.

Workup

  1. distillationAfter distilling the solvent off, the resultant crude crystal
  2. washwas washed with 1% hydrochloric acid
  3. customrecrystallized from ethyl acetate
  4. customthereby obtaining the intended substance

Sources & evidence

ORD record
ord-292370eab1f745dfb0b75aba14d801a3
Source dataset
uspto-grants-2012_11
Patent number
US08309733B2

Reaction notes

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