Pyridine → HCID 13036818, compound

HRID 2059170Notes

Reaction equation

HRID 2059170 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[SH:18].Br[CH2:20][C:21](OCC)=[O:22].N1C=CC=CC=1>C(O)CO>[F:16][C:13]([F:14])([F:15])[C:8]([C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:21](=[O:22])[CH2:20][S:18][C:3]=2[CH:4]=1)([OH:17])[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7748Ethyl bromoacetateHCID 13036817HCID 13036817, compound

Product 1

HCID 13036818HCID 13036818, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To 140 ml. of ethylene glycol is added 24 gm (0.08 mole) of 4-amino-3-mercapto[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-benzene, 14 gm. (0.08 mole) ethyl bromoacetate, and 6.4 gm. (0.08 mole) of pyridine. The solution is stirred and heated at 105°-110° for 8 hours. At the end of this period the solution is cooled and poured into 800 ml of ice-water. The resultant precipitate is filtered. The precipitate is air dried and recrystallized from ethyl acetate/hexane to give 14 gm of 7-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)-ethyl]-2H-1,4-benzothiazin-3(4H)-one, m.p. 230°-232°.

Workup

  1. temperatureheated at 105°-110° for 8 hours
  2. temperatureAt the end of this period the solution is cooled
  3. filtrationThe resultant precipitate is filtered
  4. customdried
  5. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-16e63d09d3de4787bd27ce28a912be6e
Source dataset
uspto-grants-1982_03
Patent number
US04322417

Reaction notes

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