Carbon Dioxide → N,N-dimethyl-4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetamide

HRID 1584132Notes

Reaction equation

HRID 1584132 reaction equation
[CH3:1][C:2]([CH3:22])([O:4][C:5]([NH:7][C:8]1[CH:20]=[CH:19][C:11]([O:12][CH2:13][C:14](OCC)=[O:15])=[CH:10][C:9]=1[CH3:21])=[O:6])[CH3:3].C(=O)=O.CC(O)C.[CH3:30][NH:31][CH3:32]>C(Cl)(Cl)Cl>[CH3:30][N:31]([CH3:32])[C:14](=[O:15])[CH2:13][O:12][C:11]1[CH:19]=[CH:20][C:8]([NH:7][C:5]([O:4][C:2]([CH3:22])([CH3:3])[CH3:1])=[O:6])=[C:9]([CH3:21])[CH:10]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 674Dimethylamine2×HCID 3776IsopropanolHCID 15429168Ethyl 4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetate

Product 1

HCID 15870806N,N-dimethyl-4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 100 mL pressure vessel with a stirring bar was added ethyl 4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetate (1.00 g, 3.24 mmol). The vessel was cooled in a Dry Ice®/2-propanol bath to -78° C. and dimethylamine was condensed onto the solid to a final volume of ~30 mL. The reaction vessel was sealed, allowed to warm to ambient temperature and stirred for 13 days. The excess dimethylamine was vented and the residue was dissolved in CHCl3 and concentrated, twice to remove the last traces of dimethylamine. The crude product was chromatographed on 75 g of silica gel using 75/25 EtOAC-hexane as eluant to provide 1 g (100% yield) N,N-dimethyl-4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetamide as a white, crystalline solid. 1H NMR (CDCl3): d 1.50 (s, 9H), 2.22 (s, 3H), 2.96 (s, 3H), 3.07 (s, 3H), 4.63 (s, 2H), 6.09 (br s, 1H), 6.77, (s, 2H), 7.52 (br s, 1H). ##STR51## N,N-Dimethyl 4-amino-3-methylphenoxyacetamide (5-3)

Workup

  1. customcondensed onto the solid to a final volume of ~30 mL
  2. customThe reaction vessel was sealed
  3. concentrationconcentrated
  4. customtwice to remove the last traces of dimethylamine
  5. customThe crude product was chromatographed on 75 g of silica gel using 75/25 EtOAC-hexane as eluant

Sources & evidence

ORD record
ord-7bd904e06e5a472fa357d74b2a7a58c0
Source dataset
uspto-grants-1999_08
Patent number
US05932582

Reaction notes

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