Benzyl isocyanate → HCID 89615792, compound

HRID 1747743Notes

Reaction equation

HRID 1747743 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:18])[C:12]3[CH2:13][NH:14][CH2:15][CH2:16][C:11]=3[C:10](=[O:17])[O:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:19]([N:26]=[C:27]=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[CH2:19]([NH:26][C:27]([N:14]1[CH2:15][CH2:16][C:11]2[C:10](=[O:17])[O:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=3)([CH3:18])[C:12]=2[CH2:13]1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 117901113HCID 117901113, compound

Product 1

HCID 89615792HCID 89615792, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3-hydroxyphenyl)-3-methyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (75 mg, 0.31 mmol) and benzyl isocyanate (48 μL, 0.40 mmol) in dichloromethane (5 mL) was stirred at room temperature for 1 h. The solvent was removed and the resulting residue was purified on silica to give the desired product (68 mg, 58.8%). 1H NMR (300 Hz, CDCl3) δ 1.82 (s, 3H), 2.39 (br s, 2H), 3.30-3.40 (m, 1H), 3.42-3.55 (m, 1H), 3.94 (d, J=18.0, 1H), 4.25-4.40 (m, 3H), 4.97 (t, J=6.0, 1H), 6.77-6.84 (m, 2H), 7.15-7.38 (m, 7H).

Workup

  1. customThe solvent was removed
  2. customthe resulting residue was purified on silica

Sources & evidence

ORD record
ord-1f91cd4ab54447caacf21619c4948e5d
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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