Triethylamine → HCID 9882682, compound

HRID 1250900Notes

Reaction equation

HRID 1250900 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[C:4]([CH3:17])[CH:3]=1.C(N(CC)CC)C.[C:25](Cl)(Cl)=[S:26]>C(Cl)(Cl)Cl.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:25]2=[S:26])=[C:4]([CH3:17])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 18324825HCID 18324825, compound

Product 1

HCID 9882682HCID 9882682, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of the diamine of Step A (4.8 g) and triethylamine (5.0 mL) in dry chloroform (75 mL) was added thiophosgene (2.2 mL). After 10 minutes at ambient temperature, the reaction was quenched with water and extracted with dichloromethane. The extracts were combined, dried over sodium sulfate and concentrated in vacuo to give a brown oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with 11% ethyl acetate in hexane provided a yellow solid which was triturated with diethyl ether to give the title product (2.4 g, 43.0%) as a white solid, m.p. 88-90° 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 oil
  6. customabsorbed onto a column of Merck-60 flash silica gel
  7. washElution with 11% ethyl acetate in hexane
  8. customprovided a yellow solid which
  9. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-0cfb9dcc1d994771adfd424975a01e9a
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

Loading…