Dimethylformamide → HCID 19003309, compound

HRID 2259331Notes

Reaction equation

HRID 2259331 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 50 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 50 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-01ec55f693c844a9ad3de6bc1a3a7ae2
Source dataset
uspto-grants-1995_12
Patent number
US05473001

Reaction notes

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