4-Fluorobenzoyl chloride → 2-(4-Fluorophenyl)-6-hydroxybenzothiazole

HRID 1586885Notes

Reaction equation

HRID 1586885 reaction equation
NC1C=CC(OC)=CC=1S.FC1C=CC(C(Cl)=O)=CC=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[S:29][C:30]3[CH:36]=[C:35]([O:37]C)[CH:34]=[CH:33][C:31]=3[N:32]=2)=[CH:24][CH:23]=1>>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[S:29][C:30]3[CH:36]=[C:35]([OH:37])[CH:34]=[CH:33][C:31]=3[N:32]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 2355092-Amino-5-methoxybenzene-1-thiolHCID 121799872-(4-Fluorophenyl)-6-methoxy-1,3-benzothiazole

Product 1

HCID 167341662-(4-Fluorophenyl)-6-hydroxybenzothiazole

Procedure

The procedure set out in Example 7 is repeated using 2-amino-5-methoxybenzenethiol and 4-fluorobenzoyl chloride. The reaction yields a mixture of the title compound and 2-(4-fluorophenyl)-6-methoxybenzothiazole. The mixture is treated with excess boiling 48 percent HBr for one hour to convert the latter product to the title compound. The solution is filtered and the precipitate is recrystallized from ethanol and water. The overall yield is 80.3 percent based on the initial amount of benzenethiol. A recrystallized product melts at about 221° C.-223° C.

Workup

  1. customThe reaction yields

Sources & evidence

ORD record
ord-51a11d9d083849aa852cccff0eeedb65
Source dataset
uspto-grants-1993_06
Patent number
US05216110

Reaction notes

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