Triethylamine → HCID 9817240, compound

HRID 1250897Notes

Reaction equation

HRID 1250897 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])=[C:6]([CH3:16])[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24](Cl)(Cl)=[S:25]>C(Cl)(Cl)Cl.ClCCl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:9][CH2:10][CH2:11][N:12]([CH:13]([CH3:14])[CH3:15])[C:24]2=[S:25])=[C:6]([CH3:16])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 10040ThiophosgeneHCID 18324838HCID 18324838, compound

Product 1

HCID 9817240HCID 9817240, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of the diamine of Step A (8.2 g) and triethylamine (9.09 mL) in dry chloroform (180 mL) under nitrogen was added thiophosgene (3.92 mL). After 10 minutes in the cold and 30 minutes at ambient temperature, the pH was adjusted to 8 with triethylamine and the reaction was quenched with water and extracted with dichloromethane. The combined extracts were 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 white crystalline solid which was triturated with diethyl ether to give the title product (4.5 g, 46%), m.p. 135-136° C.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined extracts were dried 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 white crystalline solid which
  9. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-01939e224490470ca1c64d32fb66749d
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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