P-Toluic Acid → HCID 7770291, compound

HRID 364880Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[F:15][C:16]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:17]=1[NH2:18]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:18][C:17]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:16]=2[F:15])=[O:10])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7470P-Toluic Acid

HCID 24386Thionyl Chloride

HCID 677752,5-Difluoroaniline

Product 1

HCID 7770291HCID 7770291, compound

Procedure

First, p-toluic acid is converted to an acid chloride with thionyl chloride. The acid chloride is reacted with 2,5-difluoroaniline to form 4-methyl-2',5'-difluorobenzanilide (V). The compound (V) is then reacted with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphethane-2,4-disulfide (Lawesson's reagent) to form 4-methyl-2',5'-difluorobenzothioanilide (VI) which is then reacted with potassium tert-butoxide to form 2-(4-methylphenyl)-5-fluorobenzothiazole (VII). The compound (VII) is then reacted with a halogenating agent such as N-bromosuccinimide, N-chlorosuccinimide or bromine to form a compound (VIII). Finally, the compound (VIII) is reacted with an excess of triethyl phosphite to produce the compound of formula (IV)-1 in which Y is a fluorine atom.

Sources & evidence

ORD record: ord-55e9e4c87397416c996e23661cbdf3f6
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04607031

Reaction notes

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