Thiophosgene → 1,3-Dichloro-2-isothiocyanatobenzene

HRID 1898296Notes

Reaction equation

HRID 1898296 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[C:10](Cl)(Cl)=[S:11].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[N:4]=[C:10]=[S:11]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 118462,6-DichloroanilineHCID 81531Diisopropylethylamine

Product 1

HCID 1232391,3-Dichloro-2-isothiocyanatobenzeneYield 39.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described for intermediate-2 using 2,6-dichloro aniline (2.0 g, 12.34 mmol), thiophosgene (1.41 g, 12.34 mmol) and N-ethyl di-isopropyl amine (7.42 g, 57.51 mmol) in DCM (20 mL) to afford 1.0 g of the desired product. 1HNMR (DMSO-d6): δ 7.62 (d, J=7.8 Hz, 2H), 7.39 (t, J=7.8 Hz, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-9a0d26eda941438985f5e1540a8d9a94
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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