Triethylamine → HCID 9857392, compound

HRID 1250896Notes

Reaction equation

HRID 1250896 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][CH2:13][CH:14]([CH3:16])[CH3:15])[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]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:25]2=[S:26])[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10040Thiophosgene2×HCID 18324831HCID 18324831, compound

Product 1

HCID 9857392HCID 9857392, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of the diamine of Step A (5.0 g) and triethylamine (5.2 mL) in dry chloroform (50 mL) under nitrogen was added thiophosgene (1.5 mL). After 5 minutes at ambient temperature, additional thiophosgene (1.0 mL) was added. After 10 minutes 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 pale brown solid which was triturated with diethyl ether to give the title product (2.8 g, 48.1%) as a white solid, m.p. 96-98° C.

Workup

  1. customAfter 10 minutes the 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 pale brown solid which
  9. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-a5eac802f85b4208aa95198e07d7198f
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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