Thiophosgene → Isothiocyanic acid, o-chlorobenzyl ester

HRID 1898336Notes

Reaction equation

HRID 1898336 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[C:10](Cl)(Cl)=[S:11].C(N(C(C)C)C(C)C)C>>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:5]=[C:10]=[S:11]

Participants

4

Reactant 3

HCID 10040ThiophosgeneHCID 666482-ChlorobenzylamineHCID 81531Diisopropylethylamine

Product 1

HCID 29351Isothiocyanic acid, o-chlorobenzyl esterYield 46.7%

Procedure

The title compound was prepared following the procedure described for Intermediate-2 using 2-chloro benzyl amine (5.0 g, 35 mmol), thiophosgene (4.38 g, 38.5 mmol) and N-ethyl di-isopropyl amine (13.5 g, 105 mmol) to afford 3.0 g of the desired product. 1HNMR (DMSO-d6): δ 5.00 (s, 2H), 7.41 (m, 2H), 7.54 (m, 2H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-df7b82d68f2e49a89a580c6d269fefd9
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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