Hydroxylamine → HCID 19063896, compound

HRID 482274Notes

Reaction equation

HRID 482274 reaction equation
[NH2:1][OH:2].[OH-].[K+].Cl[C:6]1[S:7][C:8]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:9]=2[N:10]=1>CO>[OH:2][NH:1][C:6]1[S:7][C:8]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 114704192-Chloro-6-trifluoromethylbenzothiazole

Product 1

HCID 19063896HCID 19063896, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

0.88 g of hydroxylamine hydrochloide is added to a solution of 0.7 g of potassium hydroxide in 15 ml of methanol and the reaction mixture is brought to reflux for 10 minutes. 0.5 g of 2-chloro-6-(trifluoromethyl)benzothiazole is then added and reflux is continued for 8 hours. After cooling to a temperature in the region of 20° C., the insoluble material is filtered off, the filtrate concentrated to dryness and the residue taken up in dichloromethane. The organic phase is washed with water and then dried and concentrated to dryness under reduced pressure (15 mm Hg, 2 kPa). The crude product thus obtained is purified by flash chromatography on a silica column, an ethyl acetate/cyclohexane (40/60 by volume) mixture being used as eluent. 0.35 g of 2-hydroxyamino-6-(trifluoromethyl)benzothiazole is thus obtained in the form of an orangey powder, the melting point of which is greater than 260° C. (Analysis % calculated C: 41.03, H: 2.15, N: 11.96, S: 13.69; found C: 41.4, H: 1.6, N: 12.3, S: 13.9) [1H N.M.R. spectrum (200 MHz, d6-(CD3)2SO, δ in ppm): 7.2 (broad s, 1H, aromatic CH), 7.53 (d, J=7 Hz, aromatic CH, 8.0 (broad s, 1H, aromatic CH), 10.07 (s, 1H, NH, 11.05 (s, 1H, OH)].

Workup

  1. temperatureto reflux for 10 minutes
  2. temperaturereflux
  3. filtrationthe insoluble material is filtered off
  4. concentrationthe filtrate concentrated to dryness
  5. washThe organic phase is washed with water
  6. customdried
  7. concentrationconcentrated to dryness under reduced pressure (15 mm Hg, 2 kPa)
  8. customThe crude product thus obtained
  9. customis purified by flash chromatography on a silica column

Sources & evidence

ORD record
ord-93c8d698f5854672aa332c566bbafc13
Source dataset
uspto-grants-1998_08
Patent number
US05795903

Reaction notes

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