Trifluoroacetic acid → N-(5-aminopentyl)-N-methyl-2-nitrobenzenesulfonamide

HRID 1486420Notes

Reaction equation

HRID 1486420 reaction equation
[CH3:1][N:2]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])(=[O:5])=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl.C(OC(C)C)(C)C>[NH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][N:2]([CH3:1])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86652975tert-butyl 5-(N-methyl-2-nitrophenylsulfonamido)pentylcarbamate

Product 1

HCID 58244791N-(5-aminopentyl)-N-methyl-2-nitrobenzenesulfonamideYield 99.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A solution of tert-butyl 5-(N-methyl-2-nitrophenylsulfonamido)pentylcarbamate 30d (31.5 g, 79 mmoles) and trifluoro acetic acid (29.2 mL, 5 eq) in DCM (300 mL) was stirred at RT until completion (˜16 h). The RM was then concentrated under vacuo, redissolved in DCM, washed with a saturated sodium bicarbonate aqueous solution (2 times), then brine, dried over magnesium sulfate, filtered and concentrated. Trituration in diisopropyl ether afforded 23.7 g (quantitative yield) of N-(5-aminopentyl)-N-methyl-2-nitrobenzenesulfonamide 26a as a slightly yellow solid; m/z 302 [M+H]+.

Workup

  1. concentrationThe RM was then concentrated under vacuo
  2. dissolutionredissolved in DCM
  3. washwashed with a saturated sodium bicarbonate aqueous solution (2 times)
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4bf96f75660c41a693b59e920940242b
Source dataset
uspto-grants-2016_08
Patent number
US09427440B2

Reaction notes

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