Chloroform → 1-Chloro-2-isocyano-3-methylbenzene

HRID 1702127Notes

Reaction equation

HRID 1702127 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[CH:10](Cl)(Cl)Cl.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[N+:4]#[C-:10]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 68972-Chloro-6-methylanilineHCID 14798Sodium Hydroxide

Product 1

HCID 162174661-Chloro-2-isocyano-3-methylbenzene

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

The procedure of Example 1 was again followed, using 100 g (0.7 mole) of 2-methyl-6-chloroaniline, 75 ml of chloroform, 100 ml of methylene chloride, 175 ml of 50% aqueous sodium hydroxide, and 1 g of benzyltriethylammonium chloride. The product was a solid weighing 44 g, with structure confirmed by mass spectroscopy.

Sources & evidence

ORD record
ord-8d48991346e645769c5802957fe443aa
Source dataset
uspto-grants-1983_04
Patent number
US04380468

Reaction notes

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