Ammonia → HCID 14674482, compound

HRID 2254643Notes

Reaction equation

HRID 2254643 reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[C:13]([N+:14]([O-])=O)=[CH:12][C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=1.C(O)C.Cl.N>[Fe].O>[F:18][C:2]([F:1])([F:17])[O:3][C:4]1[C:13]([NH2:14])=[CH:12][C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 702EthanolHCID 11778345HCID 11778345, compound

Product 1

HCID 14674482HCID 14674482, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

6-Trifluoromethoxy-5-nitro-2-benzothiazolamine (7.2 g), ethanol (25 cc), water (25 cc), iron powder (8.7 g) and concentrated hydrochloric acid (d=1.19) (1.1 cc) are heated to reflux for 2 hours. After returning to a temperature in the region of 20° C., the mixture is alkalinized with 28% strength ammonia solution (10 cc) and extracted 4 times with ethyl acetate (350 cc in total). The organic solution is evaporated at 50° C. under reduced pressure (20 mm Hg; 2.7 kPa). The product obtained (6.4 g) is purified by chromatography on a column of silica (800 g; particle size: 0.063-0.200 mm), eluting with an ethyl acetate/cyclohexane mixture (90:10 by volume), and recrystallized in toluene (320 cc). 6-Trifluoromethoxy-2,5-benzothiazolediamine (4 g), m.p. 175° C., is obtained.

Workup

  1. temperatureto reflux for 2 hours
  2. customAfter returning to a temperature in the region of 20° C.
  3. extractionextracted 4 times with ethyl acetate (350 cc in total)
  4. customThe organic solution is evaporated at 50° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  5. customThe product obtained (6.4 g)
  6. customis purified by chromatography on a column of silica (800 g; particle size: 0.063-0.200 mm)
  7. washeluting with an ethyl acetate/cyclohexane mixture (90:10 by volume)
  8. customrecrystallized in toluene (320 cc)

Sources & evidence

ORD record
ord-a75d02932f5a4c8abb62f59b6c1b07d4
Source dataset
uspto-grants-1993_08
Patent number
US05236940

Reaction notes

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