Triethylamine → 3-Isopropoxyphenyl isothiocyanate

HRID 2182196Notes

Reaction equation

HRID 2182196 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([CH3:3])[CH3:2].[C:12](Cl)(Cl)=[S:13].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([N:8]=[C:12]=[S:13])[CH:9]=[CH:10][CH:11]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040Thiophosgene2×HCID 5732203-(Propan-2-yloxy)aniline

Product 1

HCID 153811183-Isopropoxyphenyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-isopropoxy aniline (6.0 g, 40 mmol) in 150 ml of CHCl3 was added dropwise thiophos-gene (2.81 ml, 44 mmol) at 0° C. After the addition of thiophosgene, triethylamine (7.0 ml, 48 mmol) was added slowly and the reaction mixture was stirred for 2 hours at room temperature. It was then concentrated and diluted with 200 ml of ethyl acetate. The triethylamine hydrochloride salt was filtered off and the filtrate was concentrated to yield crude 3-isopropoxyphenyl isothiocyanate.

Workup

  1. additionwas added slowly
  2. concentrationIt was then concentrated
  3. additiondiluted with 200 ml of ethyl acetate
  4. filtrationThe triethylamine hydrochloride salt was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9e348cd67c094822b62ab53ca159cf7c
Source dataset
uspto-grants-2005_05
Patent number
US06897213B1

Reaction notes

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