N-Hydroxyphthalimide → N-Benzyloxyphthalimide

HRID 727152Notes

Reaction equation

HRID 727152 reaction equation
F[C:2](F)(F)[C:3]1[CH:4]=[C:5](CCl)[CH:6]=[CH:7][CH:8]=1.[OH:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24]>CS(C)=O>[C:3]1([CH2:2][O:13][N:14]2[C:15](=[O:24])[C:16]3=[CH:23][CH:22]=[CH:21][CH:20]=[C:17]3[C:18]2=[O:19])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 697163-(Trifluoromethyl)benzyl chloride

Product 1

HCID 255292N-Benzyloxyphthalimide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

When the bridging group n is =NOCH2 --, an appropriately substituted or unsubstituted phenylmethyl chloride, for example, 3-trifluoromethylphenylmethyl chloride, is reacted under basic conditions with N-hydroxyphthalimide in dimethyl sulfoxide, yielding the corresponding N-(phenylmethoxy)phthalimide. The so-prepared phthalimide is in turn reacted with hydrazine monohydrate in ethanol, affording an O-(phenylmethyl)hydroxylamine, for example, O-(3-trifluorophenylmethyl)hydroxylamine. The O-(phenylmethyl)hydroxylamine is then reacted with 2,4-di[(1,1-dimethylethyl)carbonylamino]-5,6,7,8-tetrahydro-6-quinazolinone, as described above, yielding the targeted 2,4-diamino-6-phenylmethoxyimino-5,6,7,8-tetrahydroquinazoline. Example 13 provides a detailed description of how this reaction is conducted.

Sources & evidence

ORD record
ord-83c2a0261c6b4bba944db82f9a1dbba5
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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