Triethylamine → HCID 9925711, compound

HRID 1250892Notes

Reaction equation

HRID 1250892 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16])[CH:2]=[CH2:3].C(N(CC)CC)C.[C:24](Cl)(Cl)=[S:25]>C(Cl)(Cl)Cl.ClCCl>[CH2:1]([N:4]1[CH2:5][CH2:6][CH2:7][N:8]([C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])[C:24]1=[S:25])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10040Thiophosgene2×HCID 18324818HCID 18324818, compound

Product 1

HCID 9925711HCID 9925711, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of the diamine of Step C (4.9 g) and triethylamine (5.8 mL) in chloroform (70 mL) under nitrogen was added thiophosgene (1.6 mL). After 20 minutes at ambient temperature, additional thiophosgene (0.5 mL) was added. After 15 minutes, the reaction was quenched with water and extracted with dichloromethane. The 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 yellow solid which was triturated with diethyl ether to give the title product (3.2 g, 55.6%) as a white solid, m.p. 82-84° C.

Workup

  1. waitAfter 15 minutes
  2. customthe reaction was quenched with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. customabsorbed onto a column of Merck-60 flash silica gel
  8. washElution with 11% ethyl acetate in hexane
  9. customprovided a yellow solid which
  10. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-d9865a805f3941059d7650253ae2f871
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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