Isatoic Anhydride → 2-(1,3-benzothiazol-2-yl)aniline

HRID 909248Notes

Reaction equation

HRID 909248 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9]12[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:14]C(=O)O[C:10]2=O>>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:10]1[C:9]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:14]

Participants

3

Reactant 2

HCID 8359Isatoic AnhydrideHCID 87132-Aminothiophenol2×

Product 1

HCID 6676802-(1,3-benzothiazol-2-yl)anilineYield 80.4%

Conditions

Temperature
140 °C

Procedure

2-Aminothiophenol (137.7 g) was heated to 110° C., and isatoic anhydride (C8H5NO3, 203.9 g) was added portionwise over a 1 h period while taking care to avoid foaming. Thereafter the temperature was raised to 140° C., and heating was continued for about 2 to 4 h until the starting material 2-aminothiophenol was consumed. The melt was poured into an enamel cuvette and after cooling, the cold material was crushed, then boiled in aqueous NaOH solution (12 g of NaOH solved in 3.5 L of water) for 2 to 3 h. The precipitate was filtered off and the filter cake was washed with cold water until the pale blue fluorescence disappeared in the washings. The precipitate was dried at 80° C. to afford 2-(benzo[d]thiazol-2-yl)phenylamine (200 g). The product was used without further purification in the next stage of preparation.

Workup

  1. temperatureheating
  2. customwas consumed
  3. additionThe melt was poured into an enamel cuvette
  4. temperatureafter cooling
  5. customthe cold material was crushed
  6. filtrationThe precipitate was filtered off
  7. washthe filter cake was washed with cold water until the pale blue fluorescence
  8. customThe precipitate was dried at 80° C.

Sources & evidence

ORD record
ord-61d93cdc6285456f8a88de3f9af239e8
Source dataset
uspto-grants-2011_09
Patent number
US08017769B2

Reaction notes

Loading…