Triethylamine → 2,6-Dichloro-4-isothiocyanatobenzonitrile

HRID 1486583Notes

Reaction equation

HRID 1486583 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([Cl:10])[C:5]([C:6]#[N:7])=[C:4]([Cl:11])[CH:3]=1.[C:12](Cl)(Cl)=[S:13].C(N(CC)CC)C>C1C=CC=CC=1>[Cl:11][C:4]1[CH:3]=[C:2]([N:1]=[C:12]=[S:13])[CH:9]=[C:8]([Cl:10])[C:5]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 596359894-Amino-2,6-dichlorobenzonitrile

Product 1

HCID 867076002,6-Dichloro-4-isothiocyanatobenzonitrileYield 71.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 4-amino-2,6-dichlorobenzonitrile (500 mg, 2.67 mmol, Eq: 1.00), thiophosgene (1.35 g, 900 μl, 11.7 mmol, Eq: 4.39), triethylamine (875 mg, 1.2 ml, 8.64 mmol, Eq: 3.23) in benzene (30 ml) was heated at reflux overnight. The brown reaction mixture was concentrated and chromatographed (80 g Analogix, 0 to 5% ethyl acetate/hexane) to give 436 mg (71%) of desired product as a light brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe brown reaction mixture was concentrated
  4. customchromatographed (80 g Analogix, 0 to 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c4b6bfec18f64e4893d1f23ecbb9a750
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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