Chloroacetyl chloride → 2-[(2-Chloroacetyl)amino]-6-methylbenzoic acid

HRID 2362272Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[Cl:12][CH2:13][C:14](Cl)=[O:15]>>[Cl:12][CH2:13][C:14]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5])=[O:15]

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 1512106-Methylanthranilic acid

Product 1

HCID 106330762-[(2-Chloroacetyl)amino]-6-methylbenzoic acid

Procedure

2-amino-6-methylbenzoic acid is reacted with 2-chloroacetyl chloride to produce the 2-(-2-chloroacetamido)-6-methylbenzoic acid. Reaction with o-toluidine and phosphoryl trichloride yields the cyclized intermediate. Further reaction with diBOC-protected adenine give the BOC protected product, which is deprotected resulting in 2-((6-amino-9H-purin-9-yl) methyl)-5-methyl-3-o-tolylquinazolin-4(3H)-one (2c).

Sources & evidence

ORD record: ord-27ff6d6b3d624ec1ab6476d8666e098d
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691829B2

Reaction notes

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