2-Chloro-6-methylaniline → 2-Chloro-6-Methylphenyl Isothiocyanate

HRID 1898307Notes

Reaction equation

HRID 1898307 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[C:10](Cl)(Cl)=[S:11].C(N(C(C)C)C(C)C)C>>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[N:4]=[C:10]=[S:11]

Participants

4

Reactant 3

HCID 68972-Chloro-6-methylanilineHCID 10040ThiophosgeneHCID 81531Diisopropylethylamine

Product 1

HCID 37317252-Chloro-6-Methylphenyl IsothiocyanateYield 27.2%

Procedure

The title compound was prepared following the procedure described for Intermediate-2 using 2-chloro-6-methylaniline (1.0 g, 0.01 mol), thiophosgene (1.15 g, 0.01 mol) and N-ethyl di-isopropyl amine (2.58 g, 0.020 mol) to afford 0.500 g of the desired product. 1HNMR (CDCl3): δ 2.39 (s, 3H), 7.10 (s, 2H), 7.21-7.25 (m, 1H); MS [M+H]+: 183.32.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-9366677f5c184a6bb86c8d550346576a
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…