Acetic Acid → HCID 66743409, compound

HRID 1467822Notes

Reaction equation

HRID 1467822 reaction equation
[CH3:1][NH:2][CH3:3].C(O)(=O)C.C=O.[CH3:10][N:11]1[C:16]2[C:17]([CH3:20])=[CH:18][NH:19][C:15]=2[C:14](=[O:21])[N:13]([CH3:22])[C:12]1=[O:23]>O>[CH3:1][N:2]([CH2:20][C:17]1[C:16]2[N:11]([CH3:10])[C:12](=[O:23])[N:13]([CH3:22])[C:14](=[O:21])[C:15]=2[NH:19][CH:18]=1)[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 66742610HCID 66742610, compound

Product 1

HCID 66743409HCID 66743409, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 50% dimethyl amine (0.4 mL), acetic acid (0.4 mL) and 38% formaldehyde (0.4 mL) were added, after which Intermediate 1 (0.4 g, 2.232 mmol) was added. The reaction mixture was refluxed for 10 min and then held for 20 min at 90° C. Reaction mixture was cooled to room temperature and diluted with water (25 mL). Two layers were separated. The aqueous layer was extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with water (25 mL), dried (Na2SO4) and filtered. The filtrate was evaporated to give a crude product which was recrystallised from acetonitrile to give 97 mg of the product as a white solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 2.08 (s, 6H), 3.23 (s, 3H), 3.30 (s, 2H), 3.69 (s, 3H), 7.13 (s, 1H), 11.93 (br s, 1H); APCI-MS (m/z) 237.00 (M+H)+.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for 10 min
  3. customReaction mixture
  4. customTwo layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×25 mL)
  6. washThe combined organic layers were washed with water (25 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated
  10. customto give a crude product which
  11. customwas recrystallised from acetonitrile

Sources & evidence

ORD record
ord-ab34d1f5591b491aa6c18d0a5a6dbb88
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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