Trifluoroacetic acid → 6-Hydroxy-2-(4-hydroxybenzoyl)benzothiazole

HRID 1075379Notes

Reaction equation

HRID 1075379 reaction equation
FC(F)(F)C(O)=O.COCCOC[O:14][C:15]1[CH:38]=[CH:37][C:18]2[N:19]=[C:20]([C:22](=[O:36])[C:23]3[CH:28]=[CH:27][C:26]([O:29]COCCOC)=[CH:25][CH:24]=3)[S:21][C:17]=2[CH:16]=1>O.CO>[OH:14][C:15]1[CH:38]=[CH:37][C:18]2[N:19]=[C:20]([C:22](=[O:36])[C:23]3[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=3)[S:21][C:17]=2[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15411537HCID 15411537, compound

Product 1

HCID 537985656-Hydroxy-2-(4-hydroxybenzoyl)benzothiazoleYield 94.8%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

0.2 ml of trifluoroacetic acid was added to a solution of 4 g of the Compound 1 obtained in Example 1 in water-methanol. The mixture was stirred for 48 hours at 70° C. After the reaction was completed, methanol was evaporated and the crystals were collected by filtration and dried to give 2.3 g of 6-hydroxy-2-(4-hydroxybenzoyl)benzothiazole (Compound 7). mp: 46° C. 1H-NMR(aceton-d6): 7.01(d,J=8.9 Hz,2H), 7.18(dd,J=8.9,2.4 Hz,1H), 7.52(d,J=2.4 Hz,1H), 8.05(d,J=8.9 Hz,1H), 8.58(d,J=8.9 Hz,2H), 9.15(br,1H), 9.40(br,1H) IR(KBr) cm-1 : 3463, 1602, 1589, 1491, 1249, 1176, 1119, 875 MS m/z: 271(M+), 243, 121 Elementary analysis (C14H9NO3S 0.8 H2O): Calculated (C=58.84,H=3.74,N=4.90); Found (C=58.78,H=3.55,N=4.54)

Workup

  1. custommethanol was evaporated
  2. filtrationthe crystals were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-a4fff1d6afac431aa706b1654b9fb541
Source dataset
uspto-grants-1999_05
Patent number
US05900426

Reaction notes

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