Acetic Acid → HCID 15434655, compound

HRID 369488Notes

Reaction equation

HRID 369488 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:14]1[O:16][CH2:15]1.[C:17](O)(=[O:19])[CH3:18]>>[OH:19][CH2:17][CH2:18][N:1]([CH2:15][CH2:14][OH:16])[C:2]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 6354Ethylene OxideHCID 10702497METHYL 2-AMINO-3,5-DIMETHYLBENZOATE

Product 1

HCID 15434655HCID 15434655, compoundYield 96%

Procedure

Methyl 2-amino-3,5-dimethylbenzoate (7.0 g, 0.039 mol) and ethylene oxide (10 g, 0.23 mol) were dissolved in 150 mL acetic acid to form a reaction mixture. The mixture was stirred at room temperature for 19 hours. and then concentrated to about 100 mL on a rotary evaporator, diluted with H2O (300 mL), and extracted with chloroform (5×200 mL). The organic extract was concentrated to give the intermediate methyl 2-bis(2'-hydroxyethyl)amino-3,5-dimethylbenzoate as an off-white oil (10.0 g, 96%). 1H NMR (300 MHz, CDCl3): 7.31 (br s, 1H), 7.16 (br s, 1H), 3.91 (s, 3H), 3.73 (m, 2H), 3.63 (m, 2H), 3.26 (br m, 4H), 2.32 (s, 3H), 2.30 (s, 3H).

Workup

  1. customto form a reaction mixture
  2. concentrationand then concentrated to about 100 mL on a rotary evaporator
  3. additiondiluted with H2O (300 mL)
  4. extractionextracted with chloroform (5×200 mL)
  5. extractionThe organic extract
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-393247f52fc24b38887e6aac82d79f6c
Source dataset
uspto-grants-2000_10
Patent number
US06137003

Reaction notes

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