Trimethylsilyl isocyanate → N-hydroxy-N-[6-(3-pyridylmethyl)-2H-1-benzopyran-3-ylmethyl]urea

HRID 1596387Notes

Reaction equation

HRID 1596387 reaction equation
C[Si]([N:5]=[C:6]=[O:7])(C)C.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][C:21]([CH2:24][NH:25][OH:26])=[CH:20][C:19]=3[CH:27]=2)[CH:9]=1>O1CCCC1>[OH:26][N:25]([CH2:24][C:21]1[CH2:22][O:23][C:18]2[CH:17]=[CH:16][C:15]([CH2:14][C:10]3[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=3)=[CH:27][C:19]=2[CH:20]=1)[C:6]([NH2:5])=[O:7]

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 15463314HCID 15463314, compound

Product 1

HCID 9904815N-hydroxy-N-[6-(3-pyridylmethyl)-2H-1-benzopyran-3-ylmethyl]ureaYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.84 ml of trimethylsilyl isocyanate was added dropwise to a solution of 3.03 g (11.3 mmol) of N-[6-(3-pyridylmethyl)-2H-1-benzopyran-3-ylmethyl]hydroxylamine in tetrahydrofuran (30 ml) at 0° C. over 5 minutes, followed by stirring overnight at room temperature. Then, the solvent was evaporated in vacuo, the residue was purified by silica gel chromatography (chloroform:methanol:concentrated ammonia water=300:9:1−100:9:1), followed by recrystallization in a mixed solvent of chloroform-methanol-ethyl acetate to obtain 2.41 g (yield=68.5%) of the desired compound as white columnar crystal.

Workup

  1. customThen, the solvent was evaporated in vacuo
  2. customthe residue was purified by silica gel chromatography (chloroform:methanol:concentrated ammonia water=300:9:1−100:9:1)
  3. customfollowed by recrystallization in a mixed solvent of chloroform-methanol-ethyl acetate

Sources & evidence

ORD record
ord-8c9184cbe47f43209c6858cec9aa1b6f
Source dataset
uspto-grants-2001_09
Patent number
US06291482B1

Reaction notes

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