4-Aminobenzonitrile → HCID 2812223, compound

HRID 2272584Notes

Reaction equation

HRID 2272584 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[S:10]([CH2:15][C:16](O)=[O:17])[CH2:11][C:12]([OH:14])=[O:13].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C1COCC1.O>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:16](=[O:17])[CH2:15][S:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:3][CH:4]=1)#[N:7]

Participants

8

Reactant 4

HCID 133964-AminobenzonitrileHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31277Thiodiglycolic acidHCID 81531Diisopropylethylamine

Product 1

HCID 2812223HCID 2812223, compoundYield 15.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-aminobenzonitrile (500 mg, 4.23 mmol), 2,2′-thiodiacetic acid (3.18 g, 21.2 mmol), WSC (4.87 g, 25.4 mmol), DMAP (258 mg, 0.21 mmol) and DIEA (5.47 g, 42.3 mmol) in THF (200 mL) was stirred at room temperature for 60 hr. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC to give 2-((2-((4-cyanophenyl)amino)-2-oxoethyl)thio)acetic acid (162 mg, 15.3%) as a pale-yellow powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with dilute hydrochloric acid
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-65d63c0180f04085ab062edf85987af1
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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