m-Tolyl isocyanate → HCID 86242638, compound

HRID 1159461Notes

Reaction equation

HRID 1159461 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]#[N:15])=[C:12]([Cl:16])[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1)=[C:18]=[O:19]>C(Cl)Cl.C1COCC1>[Cl:16][C:12]1[C:13]([C:14]#[N:15])=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:18]([NH:17][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[O:19])=[CH:7][CH:6]=2)[CH:9]=[CH:10][N:11]=1

Participants

5

Reactant 2

HCID 69303m-Tolyl isocyanate2×HCID 862425614-(4-Amino-phenyl)-2-chloro-nicotinonitrile

Product 1

HCID 86242638HCID 86242638, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 35C (0.1 g, 0.43 mmol), 1-isocyanato-3-methylbenzene (0.06 mL, 0.43 mmol) in CH2Cl2 (3 mL) and THF (3 mL) was stirred at room temperature overnight, then treated with an additional 0.02 mL of 1-isocyanato-3-methylbenzene, stirred for 5 more hours at room temperature then for 2.5 h at 50° C. The resulting precipitate was collected via filtration to give 0.1 g of the title compound. MS (ESI(+)) m/e 363 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was collected via filtration

Sources & evidence

ORD record
ord-de08fa1b5ea84ad480396cde467128b8
Source dataset
uspto-grants-2010_10
Patent number
US07812166B2

Reaction notes

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