Triethylamine → HCID 9882605, compound

HRID 1250904Notes

Reaction equation

HRID 1250904 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH:13]2[CH2:16][CH2:15][CH2:14]2)[CH:7]=1.C(N(CC)CC)C.[C:25](Cl)(Cl)=[S:26]>C(Cl)(Cl)Cl.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([N:8]2[CH2:9][CH2:10][CH2:11][N:12]([CH:13]3[CH2:16][CH2:15][CH2:14]3)[C:25]2=[S:26])[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 18324817HCID 18324817, compound

Product 1

HCID 9882605HCID 9882605, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of the diamine of Step A (3.6 g) and triethylamine (3.8 mL) in dry chloroform (40 mL) under nitrogen was added thiophosgene (1.7 mL). After 10 minutes at ambient temperature, the reaction was quenched with water and extracted with dichloromethane. The extracts were combined and dried over sodium sulfate and concentrated in vacuo to give a brown solid. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with a solvent gradient (from 11% ethyl acetate in hexane to 8:1:1 hexane-ethyl acetate-dichloromethane) provided pure material which was triturated with diethyl ether to give the title product (2.3 g, 54.9%) as a white solid, m.p. 152-154° C.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a brown solid
  6. customabsorbed onto a column of Merck-60 flash silica gel
  7. washElution with a solvent gradient (from 11% ethyl acetate in hexane to 8:1:1 hexane-ethyl acetate-dichloromethane)
  8. customprovided pure material which
  9. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-f96fcc61532d4a12868f54c863b97f26
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

Loading…