Salicylic Acid → HCID 54207586, compound

HRID 358419Notes

Reaction equation

HRID 358419 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=2[N:6]=1.[K].O[C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].CS(C)=[O:25]>C(O)(=O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([O:25][C:20]3[CH:21]=[CH:22][CH:14]=[C:15]([CH:19]=3)[C:16]([OH:18])=[O:17])=[N:6][C:5]=2[CH:7]=1

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 679Dimethyl SulfoxideHCID 5462222PotassiumHCID 103975782,5-Dichlorobenzooxazole

Product 1

HCID 54207586HCID 54207586, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Substantially equimolar amounts of 2,5-dichlorobenzoxazole and the potassium salt of 2-hydroxy benzoic acid are reacted, in an inert organic solvent, e.g., dimethylsulfoxide, in the presence of acetic acid giving 5-(5-chloro-2-benzoxazolyloxy) benzoic acid. The benzoate is then nitrated by, for example, reaction with a mixture of nitric acid, sulfuric acid and acetic anhydride to give the corresponding 2-nitrobenzoic acid prepared as previously described. The 2-nitrobenzoic acid is then reacted with ethyl 2-chloropropionate, as previously described, giving the desired 1-(ethoxycarbonyl)ethyl 5-(5-chloro-2-benzoxazolyloxy)-2-nitrobenzoate.

Sources & evidence

ORD record
ord-383d6e1b37564f7bb4a895cfc86eb016
Source dataset
uspto-grants-1984_08
Patent number
US04468244

Reaction notes

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