2-Aminothiophenol → 4-benzothiazol-2-ylbenzoic Acid

HRID 1068549Notes

Reaction equation

HRID 1068549 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)([OH:11])=[O:10].C(C(C#N)=C(C#N)C#N)#N>CC(N(C)C)=O>[C:9]([C:12]1[CH:19]=[CH:18][C:15]([C:16]2[S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:14][CH:13]=1)([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 120884-Formylbenzoic acidHCID 12635Tetracyanoethylene

Product 1

HCID 9766784-benzothiazol-2-ylbenzoic Acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-aminothiophenol (300 mg, 2.4 mmol) in DMA (3 mL) was added to resin-bound 4-carboxybenzaldehyde (subn. 0.60 mmol/g, 400 mg, 0.24 mmol), followed by TCNE (307 mg, 2.4 mmol). The suspension was shaken at 25° C. for 24h. The resin was filtered, washed with DMA and DCM, and dried under high vacuum. The resin-bound benzothiazole was cleaved from the solid support with 20% (v/v) TFA in DCM (2×5 mL, 15 min) and the combined filtrates were evaporated to give the title compound. 1H NMR (d6-DMSO) δ 7.52 (t, 1H, J=7.6 Hz), 7.60 (t, 1H, J=7.0 Hz), 8.12 (d, 2H, J=8.4 Hz), 8.23 (d, 2H, J=8.4 Hz), 8.00-8.40 (m, 2H). MS (API-ES+) m/z 256 (M+H).

Workup

  1. filtrationThe resin was filtered
  2. washwashed with DMA and DCM
  3. customdried under high vacuum
  4. customwas cleaved from the solid support with 20% (v/v) TFA in DCM (2×5 mL, 15 min)
  5. customthe combined filtrates were evaporated

Sources & evidence

ORD record
ord-25e00dbdcd6f4ac98fe6b2f903c23054
Source dataset
uspto-grants-2001_06
Patent number
US06251689B1

Reaction notes

Loading…