Butylamine → HCID 19024413, compound

HRID 1033800Notes

Reaction equation

HRID 1033800 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:13]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=1)(=[O:20])=[O:19])([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl>[CH2:1]([NH:5][CH2:33][C:30]1[CH:31]=[CH:32][C:27]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[S:18](=[O:20])(=[O:19])[NH:17][C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:28][CH:29]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 8471TriethylamineHCID 15282100[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromide

Product 1

HCID 19024413HCID 19024413, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.9 mL (2.9 g, 39.5 mmole) of n-butylamine and 1.3 mL (0.95 g, 9.4 mmole) of triethylamine in 40 mL of dry methylene chloride was added 3.39 g (7.9 mmole, based on 89% purity) of [2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl bromide (prepared as in Step D). The mixture was stirred under N2 at room temperature overnight and then concentrated to dryness. The viscous oil was dissolved in some fresh methylene chloride and evaporated onto silica gel (the minimum amount required to give a dry powder). This was layered on top of a silica gel flash column, which was eluted initially with 1:1 hexane-EtOAc and then with a larger volume of EtOAc alone. The fractions containing pure product were combined and concentrated in vacuo to yield 2.1 g (70%) of the title compound as a white solid, mp 98°-99° C., homogeneous by TLC (EtOAc); FAB-MS m/e 375 (M+1)+.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe viscous oil was dissolved in some fresh methylene chloride
  3. customevaporated onto silica gel (the minimum amount
  4. customto give a dry powder)
  5. washwas eluted initially with 1:1 hexane-EtOAc
  6. additionThe fractions containing pure product
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e7dedb7e6c246d1b7b625aedfd11b6c
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

Loading…