N,N,N',N'-Tetramethylmethanediamine → HCID 20301086, compound

HRID 1733286Notes

Reaction equation

HRID 1733286 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[CH:7]1[CH2:16][C:15](=[O:17])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:8]1)([O-:3])=[O:2].[CH3:21]N(CN(C)C)C.C(OC(=O)C)(=O)C>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[CH:7]1[C:16](=[CH2:21])[C:15](=[O:17])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:8]1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7918Acetic AnhydrideHCID 10084425HCID 10084425, compound

Product 1

HCID 20301086HCID 20301086, compound

Procedure

A mixture of 1.35 g (5 mmol) of 3'-nitroflavanone [prepared as described in J. Chem. Soc. Japan, Pure Chem. Sect. 74, 827 (1953)], and 12 ml of bis-(dimethylamino)methane was stirred at room temperature; 12 ml of acetic anhydride was added dropwise over 15 minutes. The temperature rose to 77°. After cooling to ambient temperature, the reaction was partitioned between 100 ml portions of ether and 100 ml portions of cold water. The aqueous phase was separated, washed with two 100 ml of ether, and discarded. The combined ether extracts were washed with saturated aqueous NaHCO3 solution, dried over anhydrous Na2SO4, filtered and evaporated. The residual oil was chromatographed on 100 g of silica gel, eluting with benzene to yield 548 mg of 3'-nitro-3-methylene flavanone, isolated as a white solid, m.p. 131°-132° C.

Workup

  1. customrose to 77°
  2. temperatureAfter cooling to ambient temperature
  3. customthe reaction was partitioned between 100 ml portions of ether and 100 ml portions of cold water
  4. customThe aqueous phase was separated
  5. washwashed with two 100 ml of ether
  6. washThe combined ether extracts were washed with saturated aqueous NaHCO3 solution
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residual oil was chromatographed on 100 g of silica gel
  11. washeluting with benzene

Sources & evidence

ORD record
ord-c7d6b59242294f579facfdca4aeaf05e
Source dataset
uspto-grants-1980_12
Patent number
US04241069

Reaction notes

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