Triethylamine → HCID 9857393, compound

HRID 1250906Notes

Reaction equation

HRID 1250906 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[C:6]([CH3:17])[CH:5]=[CH:4][CH:3]=1.[C:18](Cl)(Cl)=[S:19].C(N(CC)CC)C>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[C:7]([N:8]2[CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:18]2=[S:19])=[C:6]([CH3:17])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 18324821HCID 18324821, compound

Product 1

HCID 9857393HCID 9857393, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of the diamine of Step A (3.82 g) in dry chloroform (55 mL) was added dropwise at 0° C. under nitrogen triethylamine (4.18 mL) followed by thiophosgene (2.6 g). The mixture was stirred in the cold for 15 minutes and then at room temperature for 60 minutes. It was then diluted with water and after adjusting the pH to 8 with triethylamine, was extracted with dichloromethane. The combined extracts were washed with 20% aqueous sodium chloride, dried over anhydrous potassium carbonate and evaporated to dryness. The residue was flash chromatographed (on Merck-60 flash silica gel, 85:15 hexane-EtOAc) to provide 3.37 g of the title compound. Trituration and sonication with hexane and hexane-ether yielded an off-white solid (2.26 g, 51.1%), m.p. 119-121° C.

Workup

  1. waitat room temperature for 60 minutes
  2. extractionwas extracted with dichloromethane
  3. washThe combined extracts were washed with 20% aqueous sodium chloride
  4. dry with materialdried over anhydrous potassium carbonate
  5. customevaporated to dryness
  6. customchromatographed (on Merck-60 flash silica gel, 85:15 hexane-EtOAc)

Sources & evidence

ORD record
ord-a9c390b4052e491f83d5c0c79d3c6567
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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