Water → HCID 13577548, compound

HRID 653012Notes

Reaction equation

HRID 653012 reaction equation
[O:1]1[CH2:6][CH2:5][S:4][C:3]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=O)=[N:2]1.S(Cl)(Cl)=O.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][S:4][C:3]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:12])=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 24386Thionyl ChlorideHCID 13577545HCID 13577545, compound

Product 1

HCID 13577548HCID 13577548, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(5,6-Dihydro-1,4,2-oxathiazine-3-yl)benzoic acid (15 g, 0.07 mol) was suspended in methylene chloride (200 ml). Thionyl chloride (10 ml) was added and the reaction was refluxed until homogeneous and all gassing had ceased. The solvent was removed, the remaining oil was taken up in methylene chloride and treated portionwise with aniline (12.5 g, 0.12 mol). An exotherm was observed. After several hours, water was added, the organic material separated, washed successively with water, aqueous bicarbonate, dilute hydrochloric acid, water and then dried over anhydrous magnesium sulphate. Evaporation of the solvent left a solid which was recrystallised from ethanol to give crystals of 3-(5,6-dihydro-1,4,2-oxathiazin-3-yl)-N-phenylbenzamide, mp 149°-150° C. (Found: C, 64.65; H, 4.92; N, 9.65. C16H14N2O2S requires C, 64.42; H, 4.73; N, 9.39).

Workup

  1. temperaturethe reaction was refluxed until homogeneous and all gassing
  2. customThe solvent was removed
  3. waitAfter several hours
  4. customthe organic material separated
  5. washwashed successively with water, aqueous bicarbonate, dilute hydrochloric acid, water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customEvaporation of the solvent
  8. waitleft a solid which
  9. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-39bf086bc9f34e9780a20347d313b5d4
Source dataset
uspto-grants-1987_06
Patent number
US04675044

Reaction notes

Loading…