Benzene → HCID 53907020, compound

HRID 398746Notes

Reaction equation

HRID 398746 reaction equation
[CH2:1]([CH2:13][CH2:14][C:15](O)=[S:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(Cl)(=O)C(Cl)=O.C1C=CC=CC=1.[NH2:30][CH2:31][CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>O.CN(C)C(=O)C.C(N(CC)CC)C>[O:37]1[CH2:38][CH2:39][N:34]([CH2:33][CH2:32][CH2:31][NH:30][C:15](=[S:16])[CH2:14][CH2:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:35][CH2:36]1

Participants

8

Reactant 4

HCID 241Benzene2×HCID 61055N-(3-Aminopropyl)morpholineHCID 65578Oxalyl chloride2×HCID 178443143HCID 178443143, compound

Product 1

HCID 53907020HCID 53907020, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 31374DimethylacetamideSolvent

Procedure

8.23 Grams of 3-dodecylthiopropionic acid, 4.6 g of oxalyl chloride and 50 ml of benzene were charged in a flask equipped with a stirrer, a condenser and a calcium chloride drying tube and stirred for 24 hours at room temperature. After completion of the reaction, excess oxalyl chloride and benzene were distilled off under reduced pressure to prepare an acid chloride. The total of the resulting acid chloride was slowly added dropwise to 5.2 g of separately prepared N-(3-aminopropyl)morpholine, 3.7 g of triethylamine and 60 ml of N,N-dimethylacetamide which were charged in a flask. After completion of the addition, the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was introduced into 300 ml of pure water and extracted with chloroform. The chloroform layer was washed with saturated aqueous sodium chloride solution, and, then, chloroform was distilled off under reduced pressure and the residue was recrystallized from methanol to obtain 6.5 g of the desired product. m.p. 46° C.

Workup

  1. customequipped with a stirrer, a condenser and a calcium chloride drying tube
  2. distillationwere distilled off under reduced pressure
  3. customto prepare an acid chloride
  4. additionwere charged in a flask
  5. additionAfter completion of the addition
  6. stirringthe mixture was stirred at room temperature for 2 hours
  7. customAfter completion of the reaction
  8. extractionextracted with chloroform
  9. washThe chloroform layer was washed with saturated aqueous sodium chloride solution
  10. distillationchloroform was distilled off under reduced pressure
  11. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-af8d30f2d8714a889f7159d32fb0d9ae
Source dataset
uspto-grants-1998_10
Patent number
US05817599

Reaction notes

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