Acetic Acid → HCID 12340652, compound

HRID 259042Notes

Reaction equation

HRID 259042 reaction equation
[CH3:1][NH:2][CH3:3].[C:4](O)(=O)C.C=O.[CH3:10][C:11]1([CH3:24])[C:16]2=[CH:17][CH:18]=[CH:19][N:15]2[C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=2[O:12]1>C(O)C>[CH3:1][N:2]([CH2:4][C:19]1[N:15]2[C:16]([C:11]([CH3:24])([CH3:10])[O:12][C:13]3[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=32)=[CH:17][CH:18]=1)[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 12340623HCID 12340623, compound

Product 1

HCID 12340652HCID 12340652, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 18 ml of 40% aqueous dimethylamine solution and 19.8 ml of acetic acid is treated with 9 ml of 37% formalin at 10° - 15° C. The resulting solution is added at once to 10 g of 4,4-dimethyl-4H-pyrrolo[2,1-c][1,4]benzoxazine (10. g, described in Example 78) in 30 ml of ethanol. The reaction mixture is stirred at ambient temperature for 18 hr. Ethanol is removed under reduced pressure, and the remaining oily suspension is extracted with chloroform. The combined extracts are dried (Na2SO4), filtered, and evaporated to yield the title compound, nmr (CDCl3) δ 1.56 (s, 6H), 2.67 (d, J = 4.5Hz, 6H), 4.70 (d, J = 4.5Hz, 2H), 6.08 and 6.85 (d, 2H), 6.95 - 7.70 (m, 4H), 12.4 (broad, 1H).

Workup

  1. customEthanol is removed under reduced pressure
  2. extractionthe remaining oily suspension is extracted with chloroform
  3. dry with materialThe combined extracts are dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-30848c6fdb7b4b60a4f03252e18392e4
Source dataset
uspto-grants-1977_07
Patent number
US04035495

Reaction notes

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