Dimethylformamide → HCID 19003309, compound

HRID 2255729Notes

Reaction equation

HRID 2255729 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CN(C)C=O.Cl.[CH3:20][C:21]1([CH3:43])[CH2:26][CH:25]([N:27]2[C:31](=[O:32])[C:30]3=[CH:33][C:34]([C:37](Cl)=[O:38])=[CH:35][CH:36]=[C:29]3[C:28]2=[O:40])[CH2:24][C:23]([CH3:42])([CH3:41])[NH:22]1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:20][C:21]1([CH3:43])[CH2:26][CH:25]([N:27]2[C:31](=[O:32])[C:30]3=[CH:33][C:34]([C:37]([NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:38])=[CH:35][CH:36]=[C:29]3[C:28]2=[O:40])[CH2:24][C:23]([CH3:42])([CH3:41])[NH:22]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 13583DodecylamineHCID 131718103HCID 131718103, compound

Product 1

HCID 19003309HCID 19003309, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Into a 125 ml reaction flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen atmosphere were placed 2.4 g (0.013 mol) dodecylamine and 40 ml of 2% dimethylformamide in methylene chloride. This mixture was stirred during the addition of 5.0 g (0.013 mol) of the acid chloride of Example 2 accompanied by an 8° C. exotherm. The reaction mixture was cooled to ambient temperature and 2.8 g (0.028 mol) triethylamine was added, producing an exotherm of about 10° C. The reaction was allowed to stir at room temperature for 30 minutes then transferred to a separatory funnel with 50 ml methylene chloride and 50 ml water. The phases were separated and the organic phase was further extracted with three 5 ml portions of water. Additional solvent, 50 ml, was added and the organic solution washed with two 50 ml portions of 5% sodium hydroxide. The organic solution was dried with anhydrous magnesium sulfate and the solvent stripped using aspirator and high vacuum systems. The product was 6.1 g (98% of theory) of a yellow semi-solid which upon standing became a solid (melting at 42°-45° C.). The infrared spectrum (chloroform) showed two carbonyl absorptions at 1720 cm-1 (imide) and 1660 cm-1 (amide). The NMR spectrum showed the anticipated aromatic ring (7.7-7.9 ppm, doublet, 1H; 8.1-8.3, multiplet, 2H), the amide N--H (6.4-6.8 ppm, multiplet, 1H), the amide methylene (3.2-3.7 ppm, multiplet, 2H) and HALS group and amide residue [4.4-4.9 ppm, multiplet, 1H; 0.7-2.3 ppm, several multiplets].

Workup

  1. customInto a 125 ml reaction flask
  2. customequipped with a magnetic stirrer
  3. customthermometer, condenser and nitrogen atmosphere were placed
  4. customaccompanied by an 8° C.
  5. customproducing an exotherm of about 10° C
  6. customThe phases were separated
  7. extractionthe organic phase was further extracted with three 5 ml portions of water
  8. additionAdditional solvent, 50 ml, was added
  9. washthe organic solution washed with two 50 ml portions of 5% sodium hydroxide
  10. dry with materialThe organic solution was dried with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-8caf09631ace46b184a19d74de79f73c
Source dataset
uspto-grants-1993_08
Patent number
US05241067

Reaction notes

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