N-Acetylsulfanilyl chloride → N-{4-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenylsulfamoyl]-phenyl}-acetamide

HRID 1794841Notes

Reaction equation

HRID 1794841 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:18]([NH:21][C:22]1[CH:31]=[CH:30][C:25]([S:26](Cl)(=[O:28])=[O:27])=[CH:24][CH:23]=1)(=[O:20])[CH3:19]>O1CCOCC1.C(N(CC)CC)C>[O:4]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:26]([C:25]4[CH:24]=[CH:23][C:22]([NH:21][C:18](=[O:20])[CH3:19])=[CH:31][CH:30]=4)(=[O:28])=[O:27])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 222203164-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)aniline

Product 1

HCID 22220392N-{4-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenylsulfamoyl]-phenyl}-acetamideYield 43%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-phenylamine(which was obtained in Example 214) (2.8 g, 11.9 mol) in 1.4-dioxane (150 mL) and triethylamine (7 mL) was added a solution of N-acetylsulfanilyl chloride (3.5 g, 15 mmol) in 75 mL of 1,4-dioxane at room temperature. The reaction was stirred for 18 hours. The reaction mixture was concentrated. The residue was dissolved in methylene chloride and washed with diluted hydrochloric acid. The white solid in water layer was collected and dried to give the title compound as a white solid (2.5 g, 43%); 1H NMR (300 MHz, DMSO-d6) δ 1.92 (brs, 4 H), 2.06 (s, 3 H), 3.68 (brs, 4 H), 3.93 (s, 4 H), 7.06 (d, J=8.4 Hz, 2 H), 7.33 (brs, 2 H), 7.68 (d, J=9.0 Hz, 2 H), 7.71 (d, J=9.0 Hz, 2 H), 10.24 (brs, 1 H), 10.38 (s, 1 H); MS (ES) m/z: 432.3 (MH+); HRMS Calcd. for C21H25N3O5S(M+): 431.1515. Found: 431.1530.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with diluted hydrochloric acid
  4. customThe white solid in water layer was collected
  5. customdried

Sources & evidence

ORD record
ord-95d80d411c21485c995d1420a2c663b5
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

Loading…