Oxalyl chloride → HCID 86609826, compound

HRID 1096472Notes

Reaction equation

HRID 1096472 reaction equation
C(Cl)(=O)C([Cl:4])=O.[Cl:7][C:8]1[CH:16]=[C:15]([O:17][CH2:18][C@@H:19]2[CH2:24][N:23]([CH3:25])[C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[O:20]2)[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].OC1C=CC(C(OC)=O)=C(Cl)C=1>CN(C)C=O.COCCOC>[Cl:7][C:8]1[CH:16]=[C:15]([O:17][CH2:18][C@@H:19]2[CH2:24][N:23]([CH3:25])[C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[O:20]2)[CH:14]=[CH:13][C:9]=1[C:10]([Cl:4])=[O:11]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 134988302-Chloro-4-hydroxy-benzoic acid methyl esterHCID 66781739HCID 66781739, compound

Product 1

HCID 86609826HCID 86609826, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under argon atmosphere, oxalylchloride (0.3 mL) and N,N-dimethylformamide (1 drop) were added to a solution (4.5 mL) of 2-chloro-4-(((2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy)benzoic acid (488 mg: the compound produced by the same procedures as a series of Example 8→Example 9→Example 10 using methyl 4-hydroxy-2-chlorobenzoate instead of the compound produced in Example 3.) in 1,2-dimethoxyethane, which was stirred for 1 hour at 40° C. The title compound was obtained by concentrating the reaction mixture.

Sources & evidence

ORD record
ord-4d2b6f9d9b4f4d08b34d6521b1f119b3
Source dataset
uspto-grants-2012_03
Patent number
US08138335B2

Reaction notes

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