m-(Trifluoromethyl)benzamide → 5-(alpha,alpha,alpha-Trifluoro-m-Tolyl)-1,3,4-Oxathiazol-2-One

HRID 443701

Reaction equation

HRID 443701 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([NH2:11])=[O:10])[CH:4]=1.Cl[C:15]([S:17]Cl)=[O:16]>C(OCC)(=O)C>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[O:10][C:15](=[O:16])[S:17][N:11]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 74535m-(Trifluoromethyl)benzamideHCID 75990(Chlorothio)formyl chloride

Product 1

HCID 122601105-(alpha,alpha,alpha-Trifluoro-m-Tolyl)-1,3,4-Oxathiazol-2-OneYield 86.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

α,α,α-Trifluoro-m-toluamide (82.7 g, 0.437 mol) and chlorocarbonylsulfenyl chloride (86 g, 0.667 mol, 53% excess) were reacted under the conditions of Example 2 for 0.5 hours. The light yellow residue was dissolved in ethyl acetate and cooled to -78°. The white precipitate was filtered and washed with hexane to yield 93.14 g (0.377 mol, 86.2%) of white solid, m.p. 85°-86.5°.

Workup

  1. temperaturecooled to -78°
  2. filtrationThe white precipitate was filtered
  3. washwashed with hexane

Sources & evidence

ORD record
ord-745498c25ccc40d08310b90c6e84aa74
Source dataset
uspto-grants-1981_04
Patent number
US04261728

Linked notes

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