Diethyl Oxalate → HCID 21137088, compound

HRID 1244348Notes

Reaction equation

HRID 1244348 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:15][C:14]=1[NH2:25]>>[CH2:9]([O:8][C:1](=[O:7])[C:2]([NH:25][C:14]1[CH:15]=[C:16]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[CH:17]=[CH:18][C:13]=1[O:12][CH3:11])=[O:4])[CH3:10]

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 113677782-Methoxy-5-morpholinoaniline

Product 1

HCID 21137088HCID 21137088, compoundYield 77%

Conditions

Temperature
180 °C

Procedure

139 ml (1015 mmol) Diethyl oxalate was heated to 120° C. 30.3 g (145 mmol) 2-methoxy-5-morpholin-4-yl-phenylamine was added very cautiously in small quantities and the mixture was heated for 90 minutes at 180° C. After cooling to room temperature and filtration 1.5 n-hexane were added. The resulting precipitate was collected by filtration. After washing with hexane and drying, 34.4 g (77%) N-(2-methoxy-5-morpholin-4-yl-phenyl)-oxalamic acid ethyl ester was obtained as greenish crystals, M.p.: 95–97° C., MS m/e (%): 309 (M+H+, 100).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltration 1.5 n-hexane
  3. additionwere added
  4. filtrationThe resulting precipitate was collected by filtration
  5. washAfter washing with hexane
  6. customdrying

Sources & evidence

ORD record
ord-cd35805ceb3243daae4e908c4d807623
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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