Triethylamine hydrochloride → HCID 178427888, compound

HRID 1265164Notes

Reaction equation

HRID 1265164 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([C:9]#[N:10])[C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=1[CH3:19].[N-:20]=[N+:21]=[N-:22].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([C:9]2[NH:22][N:21]=[N:20][N:10]=2)[C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=1[CH3:19]

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 12045115HCID 12045115, compound

Product 1

HCID 178427888HCID 178427888, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

[2,3-Difluoro-6-cyano-phenyl]-(4-iodo-2-methyl-phenyl)-amine (1.11 g, 3 mmol) and Sodium azide(0.255 g, 3.9 mmol) and triethylamine hydrochloride (0. 537 g, 3.9 mmol) were all suspended in 10 ml toluene and stirred at 100° C. for 12 hours. The mixture was concentrated and the residue purified by column chromatography with ethyl acetate/methanol (10/1) to give the product as a foam-like solid. The yield: ˜50% m.p: 83.4-88.7° C. 1H NMR(CDCl3, 400 Hz): δ/ppm 7.69(1H, m, Phenyl-H); 7.42(1H, s, Phenyl-H); 7.27(1H, m, Phenyl-H); 6.91(1H, dd, J=16.2 Hz, 8.3 Hz, Phenyl-H); 6.40(1H, dd, Phenyl-H); 2.28(3H, s, CH3)

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified by column chromatography with ethyl acetate/methanol (10/1)

Sources & evidence

ORD record
ord-e4346d745fd141588887a9e90494faac
Source dataset
uspto-grants-2003_04
Patent number
US06545030B1

Reaction notes

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