Ammonia → N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamide

HRID 2306865Notes

Reaction equation

HRID 2306865 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][CH2:12][CH3:13])=[CH:7][C:6]=2[CH:14]=1.O1CCCC1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].N>O.C(OC)(C)(C)C>[CH2:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:14][C:6]=2[CH:7]=1)[CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chloride2×HCID 98133112-Butylbenzofuran-5-amine

Product 1

HCID 9878493N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamideYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

100 g of 5-amino-2-butylbenzofuran, 192 ml of tetrahydrofuran and 96 ml of methyl tert-butyl ether are introduced into a round-bottomed flask. 59.35 g of methanesulfonyl chloride are added, at 20° C., followed by 43.23 g of 20% aqueous ammonia. 44.51 g of methanesulfonyl chloride are then introduced, followed by 86.47 g of 20% aqueous ammonia. 48 ml of water are then added, the medium is separated by settling and the organic phase is washed twice with 211 g of 10% aqueous sodium chloride solution. The medium is separated by settling and concentrated at 400° C. under vacuum, to give the desired compound in crude form (weight yield: 100%).

Workup

  1. customthe medium is separated
  2. washthe organic phase is washed twice with 211 g of 10% aqueous sodium chloride solution
  3. customThe medium is separated
  4. concentrationconcentrated at 400° C. under vacuum

Sources & evidence

ORD record
ord-48de0d6779d247bebfba6cac289551a4
Source dataset
uspto-grants-2004_12
Patent number
US06828448B2

Reaction notes

Loading…