Benzaldehyde → 2-(4-(benzylamino)-3-iodophenyl)-N-methylethane-1-sulfonamide

HRID 1028413Notes

Reaction equation

HRID 1028413 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([I:15])[CH:9]=1)(=[O:5])=[O:4].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+].C(O)(C)C>CO>[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]([I:15])[CH:9]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 669737042-(4-amino-3-iodophenyl)-N-methylethanesulfonamide

Product 1

HCID 669737022-(4-(benzylamino)-3-iodophenyl)-N-methylethane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 2-(4-amino-3-iodo-phenyl)-ethanesulfonic acid methylamide (100 g) in anhydrous methanol (500 ml), a solution of benzaldehyde (46 g) in methanol (100 ml) was added dropwise maintaining temperature below 30° C. The reaction mass was stirred for 2-3 hours at 25° C. and sodium borohydride (12 g) was added over a period of 2 hours maintaining the temperature below 30° C. The reaction mass was stirred for about 2 hours at 25° C. Methanol was evaporated from the mixture and water (1000 ml) was added. The solution was extracted with dichloromethane (2000 ml). The organic layer was washed with water and distilled under vacuum to obtain a solid. The solid was treated with isopropyl alcohol (500 ml), filtered and dried under vacuum at 50-55° C. to obtain the title compound. (Yield: 116 g, HPLC Purity: 99%)

Workup

  1. temperaturemaintaining temperature below 30° C
  2. temperaturemaintaining the temperature below 30° C
  3. stirringThe reaction mass was stirred for about 2 hours at 25° C
  4. customMethanol was evaporated from the mixture and water (1000 ml)
  5. additionwas added
  6. extractionThe solution was extracted with dichloromethane (2000 ml)
  7. washThe organic layer was washed with water
  8. distillationdistilled under vacuum
  9. customto obtain a solid
  10. filtrationfiltered
  11. customdried under vacuum at 50-55° C.

Sources & evidence

ORD record
ord-7499d528c37e469892a41aeb1aed9d4e
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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