Benzyl isocyanate → HCID 70430381, compound

HRID 542279Notes

Reaction equation

HRID 542279 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:11]([NH:18][CH:19]1[CH:23]=[CH:22][S:21](=[O:25])(=[O:24])[CH2:20]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1C=CC=CC=1>[CH2:1]([NH:8][C:9]([N:18]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:19]1[CH:23]=[CH:22][S:21](=[O:25])(=[O:24])[CH2:20]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 3152854HCID 3152854, compound

Product 1

HCID 70430381HCID 70430381, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Benzylisocyanate (2.26 g, 17.0 mmol, 135 mol %) was added to a mixture of amine 3 (2.80 g, 12.6 mmol) in a benzene (75 mL). After 10 hr of reflux, the solution was cooled and filtered, and the solvent was evaporated from the filtrate to afford the crude product (3.29 g, 74% yield). A portion was purified by column chromatography on silica gel with dichloromethane-ethyl acetate. 1H N NMR (CDCl3) δ 1.7 (1H, s, NH), 3.02 (1H, dd, CHSO2), 3.65 (1H, dd, CHSO2), 4.4 (4H, m, CH2Ph), 4.95, (1H, m, CHN), 6.57 (2H, m, CH=CH), 7.23 (10H, s, arom).

Workup

  1. temperatureAfter 10 hr of reflux
  2. temperaturethe solution was cooled
  3. filtrationfiltered
  4. customthe solvent was evaporated from the filtrate

Sources & evidence

ORD record
ord-3eb8667f6af84708a961c92869bbb272
Source dataset
uspto-grants-1987_04
Patent number
US04656289

Reaction notes

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