HCID 13416380, compound → HCID 49869281, compound

HRID 570970Notes

Reaction equation

HRID 570970 reaction equation
[N:1]([CH2:4][S:5][CH3:6])=[C:2]=[O:3].[N+:7](=[C:9]1[C:13](/[CH:14]=[CH:15]/[C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)=[N:12][CH:11]=[N:10]1)=[N-:8]>CS(C)=O>[CH3:6][S:5][CH2:4][N:1]1[C:2](=[O:3])[N:10]2[CH:11]=[N:12][C:13](/[CH:14]=[CH:15]/[C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)=[C:9]2[N:7]=[N:8]1

Participants

4

Reactant 2

HCID 13416380HCID 13416380, compoundHCID 86663794HCID 86663794, compound

Product 1

HCID 49869281HCID 49869281, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of (isocyanatomethyl)(methyl)sulfane (337 mg, 3.27 mmol) in dry DMSO (1 mL) 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 and diethyl ether. The crude product was dried under vacuum and was absorbed on silica and purified by flash chromatography using DCM:MeCN (95:5) as eluent to give the pure title compound as a bright yellow solid (71 mg, 8%). δH (DMSO d6): 8.87 (1H, s), 7.94-7.97 (2H, d, J=8.6), 7.85-7.87 (2H, d, J=8.6), 7.73 (2H, s), 5.40 (2H, s), 2.27 (3H, s).

Workup

  1. additionThe resulting solution was poured into ice
  2. filtrationthe precipitate was filtered
  3. washwashed successively with water 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-fd49bf2185c4414a94297543dd735972
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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