Triethylamine → HCID 21461086, compound

HRID 1941444Notes

Reaction equation

HRID 1941444 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH2:5]([N:7]([CH2:14][CH2:15][CH2:16][NH2:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:6].C(N(CC)CC)C>C(Cl)Cl>[CH2:5]([N:7]([CH2:14][CH2:15][CH2:16][N:17]=[C:1]=[S:2])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 315219753606-48-7

Product 1

HCID 21461086HCID 21461086, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of thiophosgene (7.43 ml) in CH2Cl2 (300 ml) was added dropwise over 11/2 hours at 20° C. under a nitrogen atmosphere to a stirred solution of N-ethyl-N-(3-aminopropyl)aniline (17.8 g) and triethylamine (27.8 ml) in CH2Cl2 (500 ml). The mixture was stirred at 20° C. for a further 11/2 hours then heated under reflux for 11/2 hours. The mixture was allowed m cool washed with water, dried over MgSO4, filtered and solvent removed from the filtrate in vacuo. The product was purified by chromatography on silica gel eluting with CH2Cl2 to give N-ethyl-N-(3-isothiocyanatopropyl)aniline (72 g) as a red oil.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 11/2 hours
  3. temperaturecool
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customsolvent removed from the filtrate in vacuo
  8. customThe product was purified by chromatography on silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-f0a341d9b1c04104be7972bc29284dc9
Source dataset
uspto-grants-1997_12
Patent number
US05703215

Reaction notes

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