Hydrochloric Acid → HCID 22097108, compound

HRID 861517Notes

Reaction equation

HRID 861517 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][CH2:13][C:14]([OH:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:12][CH2:13][C:14]([OH:16])=[O:15])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 11430Potassium CarbonateHCID 118992,4-Dichloronitrobenzene

Product 1

HCID 22097108HCID 22097108, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25 g (0.13 mol) of 2,4-dichloro-1-nitrobenzene, 19.5 g (0.26 mol) of glycine and 18 g (0.13 mol) of potassium carbonate were heated in 200 ml of dimethylformamide at 120° C. for 3 h. The mixture was then poured into ice-water, acidified with 1M hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase: toluene/acetone/acetic acid=20:10:1) to yield 19.7 g (66%) of the product. Melting point 147°-148° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (mobile phase: toluene/acetone/acetic acid=20:10:1)

Sources & evidence

ORD record
ord-e55298b7e696403ca9f320b1bbc47f5c
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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