Chlorosulfonic acid → HCID 59591401, compound

HRID 1666570Notes

Reaction equation

HRID 1666570 reaction equation
[CH:1]1([C:6]2[S:10][C:9]([NH:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])=[N:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[S:21]([Cl:25])(=O)(=[O:23])[OH:22]>[OH-].[Na+]>[CH:1]1([C:6]2[S:10][C:9]([NH:11][C:12]([C:13]3[CH:18]=[C:17]([S:21]([Cl:25])(=[O:23])=[O:22])[CH:16]=[CH:15][C:14]=3[F:19])=[O:20])=[N:8][N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 856742HCID 856742, compound2×

Product 1

HCID 59591401HCID 59591401, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
200 °C

Procedure

3-{[(5-cyclopentyl-1,3,4-thiadiazol-2-yl)amino]carbonyl}-4-fluorobenzenesulfonyl chloride was prepared from N-(5-cyclopentyl-1,3,4-thiadiazol-2-yl)-2-fluorobenzamide using a Biotage Initiator 8 microwave set to high absorbance as follows. Using conditions described, the reaction reached a pressure of 12 barr. The pressure was reduced to 3 barr after cooling and was vented prior to decapping the reaction vessel. To a 5 ml Biotage microwave reaction tube was added N-(5-cyclopentyl-1,3,4-thiadiazol-2-yl)-2-fluorobenzamide (0.305 g, 1.05 mmol) and a Teflon covered magnetic stir-bar. To this was added 2 ml of chlorosulfuric acid. The vessel was capped and heated to 200° C. for 3.25 min. After cooling to room temperature, the remaining pressure was vented into a 50 ml syringe and discharged into 30 ml 1M NaOH. Reaction was quenched by adding dropwise to 30 ml of crushed ice-water while stirring. The solid product was collected by vacuum filtration, washed with water (5 ml, 3×) and air-dried under vacuum, yielding 3-{[(5-cyclopentyl-1,3,4-thiadiazol-2-yl)amino]carbonyl}-4-fluorobenzenesulfonyl chloride as a off white solid (290 mg, 71%), Crude product was used to next step.

Workup

  1. temperatureafter cooling
  2. customTo a 5 ml Biotage microwave reaction tube
  3. customThe vessel was capped
  4. temperatureAfter cooling to room temperature
  5. customthe remaining pressure was vented into a 50 ml syringe
  6. customReaction
  7. customwas quenched
  8. additionby adding dropwise to 30 ml of crushed ice-water
  9. filtrationThe solid product was collected by vacuum filtration
  10. washwashed with water (5 ml, 3×)
  11. customair-dried under vacuum

Sources & evidence

ORD record
ord-2a9e924385474036be5abe420d1ab613
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

Loading…