Triethylamine → HCID 9925710, compound

HRID 1250885Notes

Reaction equation

HRID 1250885 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[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[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[CH3:16])[C:24]1=[S:25])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 10040ThiophosgeneHCID 18324837HCID 18324837, compound

Product 1

HCID 9925710HCID 9925710, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of the diamine of Step C (3.4 g) and triethylamine (4.0 mL) in dry chloroform (50 mL) was added dropwise under nitrogen thiophosgene (1.1 mL). After 30 minutes at ambient temperature, additional triethylamine (1.0 mL) and thiophosgene (0.28 mL) were added. After 15 minutes, no starting material remained. The reaction was quenched with water, the pH adjusted to 8 with triethylamine, 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 10% ethyl acetate in hexane provided a yellow solid which was triturated with diethyl ether to give the title compound (1.69 g, 42.4%) as a white solid, m.p. 71-72° C.

Workup

  1. waitAfter 15 minutes
  2. customThe reaction was quenched with water
  3. extractionextracted with dichloromethane
  4. dry with materialdried 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 10% ethyl acetate in hexane
  9. customprovided a yellow solid which
  10. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-d05bd6d99beb4ed0b1d589bb0b364a1d
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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