Hydrochloric Acid → HCID 19917419, compound

HRID 1756258Notes

Reaction equation

HRID 1756258 reaction equation
[NH2:1][N:2]1[C:7]2[CH:8]=[C:9]([S:12]([C:15]([F:27])([F:26])[C:16]([F:25])([F:24])[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])(=[O:14])=[O:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:29])([CH3:28])[CH2:3]1.Cl[C:31]([O:33][CH3:34])=[O:32].Cl>N1C=CC=CC=1>[CH3:28][C:4]1([CH3:29])[CH2:3][N:2]([NH:1][C:31]([O:33][CH3:34])=[O:32])[C:7]2[CH:8]=[C:9]([S:12]([C:15]([F:27])([F:26])[C:16]([F:24])([F:25])[C:17]([F:22])([F:23])[C:18]([F:19])([F:20])[F:21])(=[O:14])=[O:13])[CH:10]=[CH:11][C:6]=2[O:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 19917414HCID 19917414, compound

Product 1

HCID 19917419HCID 19917419, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4-Dihydro-4-amino-2,2-dimethyl-6-(nonafluorobutyl)sulfonyl-2H-1,4-benzoxazine (0.46 g) was dissolved in 5 ml of pyridine, followed by the dropwise addition of 0.12 ml of methyl chloroformate under ice cooling and stirring. After the reaction mixture was stirred for 15 hours at room temperature, the reaction mixture was added with 10% hydrochloric acid and then extracted twice with chloroform. The combined chloroform layer was washed with water and with saturated brine and was then dried over magnesium sulfate. The solvent was distilled off and the residue was purified by chromatography on a silica gel column, whereby 0.77 g of Compound No. 53 was obtained (yield: 70 %).

Workup

  1. stirringAfter the reaction mixture was stirred for 15 hours at room temperature
  2. extractionextracted twice with chloroform
  3. washThe combined chloroform layer was washed with water and with saturated brine
  4. dry with materialwas then dried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by chromatography on a silica gel column, whereby 0.77 g of Compound No
  7. custom53 was obtained (yield: 70 %)

Sources & evidence

ORD record
ord-6836d783f97b4a71afd7866d24941958
Source dataset
uspto-grants-1995_08
Patent number
US05440036

Reaction notes

Loading…