Water → 5-Hexylsulfonamido-2-methylbenzoxazole

HRID 1199328Notes

Reaction equation

HRID 1199328 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.[CH2:12]([S:18](Cl)(=[O:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].O>N1C=CC=CC=1>[CH2:12]([S:18]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1)(=[O:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 845041-Hexanesulfonyl chlorideHCID 7379202-Methyl-1,3-benzoxazol-5-amine

Product 1

HCID 150510645-Hexylsulfonamido-2-methylbenzoxazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 29.6 g of 5-amino-2-methylbenzoxazole in 100 ml pyridine cooled to 0° C. was added 41.3 g hexanesulfonyl chloride. After 1 hour stirring at 0° C., a reddish precipitate formed. The reaction mixture was stirred at room temperature for 2 days and then poured into 1.4 l of water and stirred for 2 hours. A heavy oil deposited and the supernatant was decanted. The oil was dissolved in 1.0 l dichloromethane, which was extracted with 4×200 ml of 1N hydrochloric acid, then dried over magnesium sulfate. The solvent was removed, leaving a reddish brown liquid of 5-hexylsulfonamido-2-methylbenzoxazole (Intermediate A).

Workup

  1. customa reddish precipitate formed
  2. stirringThe reaction mixture was stirred at room temperature for 2 days
  3. stirringstirred for 2 hours
  4. customthe supernatant was decanted
  5. dissolutionThe oil was dissolved in 1.0 l dichloromethane
  6. extractionwhich was extracted with 4×200 ml of 1N hydrochloric acid
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-3544c1be2b674f4f893f86e3dcf60a83
Source dataset
uspto-grants-1990_02
Patent number
US04900653

Reaction notes

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