Hydroxyamine hydrochloride → 6-(Anilinosulfonyl)-N-hydroxyhexanamide

HRID 226180Notes

Reaction equation

HRID 226180 reaction equation
[NH:1]([S:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=O)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:22][OH:23].C[O-].[Na+]>CO>[NH:1]([S:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:22][OH:23])=[O:18])(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 22492477HCID 22492477, compound

Product 1

HCID 99005256-(Anilinosulfonyl)-N-hydroxyhexanamideYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of ethyl 6-(anilinosulfonyl)hexanoate (64b) and hydroxylamine hydrochloride (0.43 g, 6.2 mmol) in methanol (5 ml) the 3.43 N solution of sodium methylate (2.62 ml, 9.0 mmol) in methanol was added and the reaction was stirred at ambient temperature for 40 min. The reaction mixture was poured into saturated NaH2PO4 (15 ml) and extracted with ethyl acetate. The extract was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was evaporated, the residue was washed with diethyl ether and crystallised from ethyl acetate. The title compound (0.3 g, 69%) was obtained as white crystals, m.p. 97-98° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.02-1.78 (m, 6H, CH2); 1.90 (br t, 2H, J=6.4 Hz, CH2); 3.06 (t, 2H, J=7.0 Hz, CH2); 6.94-7.60 (m, 5H, arom.); 8.66 (br s, 1H, NH); 9.76 (br s, 1H, NH), 10.36 (br s, 1H, OH). HPLC analysis on Symmetry C8 column: impurities 3.5% (column size 3.9×150 mm; mobile phase acetonitrile—0.1M phosphate buffer (pH 2.5), 30:70; detector UV 220 nm; flow rate 1.1 ml/min; sample concentration 0.4 mg/ml). Anal. Calcd for C12H18N2O4S, %: C 50.33, H 6.34, N 9.78, S 11.20. Found, %: C 50.10, H 6.22, N 9.83, S 11.10.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. washthe residue was washed with diethyl ether
  7. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-34629a2363a441a594d35b8674853aa0
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

Loading…