Triethylamine → HCID 23447830, compound

HRID 1840380Notes

Reaction equation

HRID 1840380 reaction equation
[Cl:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](Cl)(Cl)=[S:11].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[N:4]=[C:10]=[S:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 888842-Chloro-3-fluoroaniline

Product 1

HCID 23447830HCID 23447830, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a solution of 2-chloro-3-fluoroaniline (2.61 g, 17.94 mmol) in 50 mL of toluene at room temperature, thiophosgene (2.1 mL, 26.91 mmol) and triethylamine (3.02 mL, 26.91 mmol) was added. The mixture was stirred at room temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The combined organic layer was then concentrated to give the desired product (2.99 g, 89%). 1H NMR (CDCl3) δ 7.10 (m, 1H), 7.22 (m, 1H).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. concentrationThe combined organic layer was then concentrated

Sources & evidence

ORD record
ord-44095e62972c4060b14dce4d6f4b83f2
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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