Iodine → HCID 67017185, compound

HRID 2406201Notes

Reaction equation

HRID 2406201 reaction equation
II.[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([S:14][CH3:15])[NH:8][C:7]2=O.[N+:17]([C:20]1[N:24]=[CH:23][NH:22][N:21]=1)([O-:19])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1>[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([S:14][CH3:15])[N:8]=[C:7]2[N:22]1[CH:23]=[N:24][C:20]([N+:17]([O-:19])=[O:18])=[N:21]1

Participants

7

Reactant 5

HCID 807IodineHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 135471382HCID 135471382, compoundHCID 178526901HCID 178526901, compound

Product 1

HCID 67017185HCID 67017185, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Iodine (16.5 g, 65.1 mmol) was added to a suspension of compound 5a (8.03 g, 29.6 mmol), 3-nitro-1H-1,2,4-triazole (11.8 g, 103.6 mmol), triphenylphosphine (18.1 g, 69.1 mmol) in 630 mL of toluene. The reaction mixture was rapidly heated to 95° C. for 15 minutes after which 25 mL of N,N-diisopropylethylamine was added and the mixture was stirred for another 50 minutes. The reaction was cooled to room temperature and concentrated under reduced pressure. The crude product was precipitated from ethanol, to give 6 as a yellow solid (9.67 g, 89%). mp: 204° C.,

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was precipitated from ethanol

Sources & evidence

ORD record
ord-55e9cdb1b93c4715956d0ff91a501923
Source dataset
uspto-grants-2014_08
Patent number
US08809355B2

Reaction notes

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