Dimethylacetamide → HCID 54008544, compound

HRID 398745Notes

Reaction equation

HRID 398745 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.CN(C)C(=O)C.[CH2:16]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](Cl)=[S:37])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C1C=CC=CC=1>[O:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][C:36](=[S:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 4082852-MorpholinoethylamineHCID 54146617HCID 54146617, compound

Product 1

HCID 54008544HCID 54008544, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.6 Grams of N-(2-aminoethyl)morpholine and 30 ml of N,N-dimethylacetamide were charged in a flask equipped with a stirrer, a condenser and a calcium chloride drying tube and stirred with ice cooling. To the resulting solution was slowly added dropwise 7.5 g of 11-decylthioundecanoic acid chloride. After completion of the addition, the temperature of the solution was returned to room temperature, followed by further stirring for 2 hours. The reaction mixture was diluted with 300 ml of benzene, and washed with 5% aqueous sodium bicarbonate solution, pure water and saturated aqueous sodium chloride solution in succession. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to obtain a crystal. The crystal was recrystallized from n-hexane to obtain 7.3 g of the desired product. m.p. 80° C.

Workup

  1. customequipped with a stirrer, a condenser and a calcium chloride drying tube
  2. additionAfter completion of the addition
  3. customwas returned to room temperature
  4. stirringby further stirring for 2 hours
  5. washwashed with 5% aqueous sodium bicarbonate solution, pure water and saturated aqueous sodium chloride solution in succession
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain a crystal
  9. customThe crystal was recrystallized from n-hexane

Sources & evidence

ORD record
ord-fa429e5e95ee43c0a043ed025220e8a1
Source dataset
uspto-grants-1998_10
Patent number
US05817599

Reaction notes

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