1161826-12-5 → HCID 49868654, compound

HRID 570971Notes

Reaction equation

HRID 570971 reaction equation
[N:1]([CH2:4][S:5]([CH3:8])(=[O:7])=[O:6])=[C:2]=[O:3].[N+:9](=[C:11]1[C:15]([CH:16]=[CH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)=[N:14][CH:13]=[N:12]1)=[N-:10]>CS(C)=O>[CH3:8][S:5]([CH2:4][N:1]1[C:2](=[O:3])[N:12]2[CH:13]=[N:14][C:15](/[CH:16]=[CH:17]/[C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)=[C:11]2[N:9]=[N:10]1)(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 595674581161826-12-5HCID 86663796HCID 86663796, compound

Product 1

HCID 49868654HCID 49868654, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Isocyanato(methylsulfonyl)methane (440 mg, 3.25 mmol) was added dropwise in the dark under nitrogen to a stirred suspension of E)-4-(2-(4-diazo-4H-imidazol-5-yl)vinyl)benzonitrile (600 mg, 2.71 mmol) in DMSO (6 mL) and the mixture was stirred overnight. The resulting solution was poured into ice and the precipitate was filtered and washed successively with water, ethyl acetate and diethyl ether. The crude product was dried under vacuum and was absorbed on silica and purified by flash chromatography using DCM:MeCN (90:10) as eluent to give the pure title compound as a bright yellow solid (31 mg, 3% yield). δH (DMSO d6): 8.95 (1H, s), 7.95-7.97 (2H, d, J=8.6), 7.84-7.87 (2H, d, J=8.6), 7.75 (2H, s), 5.76 (2H, s), 3.16 (3H, s).

Workup

  1. additionThe resulting solution was poured into ice
  2. filtrationthe precipitate was filtered
  3. washwashed successively with water, ethyl acetate and diethyl ether
  4. dry with materialThe crude product was dried under vacuum
  5. customwas absorbed on silica
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e82532c5dc0a4c8d990d2d2f46718b01
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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