Chlorosulfamic acid → HCID 66746802, compound

HRID 1467233Notes

Reaction equation

HRID 1467233 reaction equation
[NH2:1][C:2]1[C:3]([C:19]#[N:20])=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][CH2:6][C:7]([CH3:15])([CH3:14])[C:8]([NH:10][CH2:11][CH2:12][CH3:13])=[O:9].[S:21](Cl)(=[O:24])(=[O:23])[NH2:22]>CC(N(C)C)=O.CCOC(C)=O>[S:21]([NH:1][C:2]1[C:3]([C:19]#[N:20])=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][CH2:6][C:7]([CH3:15])([CH3:14])[C:8]([NH:10][CH2:11][CH2:12][CH3:13])=[O:9])(=[O:24])(=[O:23])[NH2:22]

Participants

5

Reactant 2

HCID 24499Chlorosulfamic acidHCID 468336623-(3-Amino-2-cyanophenoxy)-2,2-dimethyl-N-propylpropanamide

Product 1

HCID 66746802HCID 66746802, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-(3-amino-2-cyanophenoxy)-2,2-dimethyl-N-propylpropanamide (16.5 g, 59.92 mmol) (Example 197b) in DMA (50 mL) was added sulfamoyl chloride (13.85 g, 119.84 mmol) at 0° C. under nitrogen. The reaction mixture was then stirred at room temperature under nitrogen for 3 hrs then diluted with EtOAc, washed successively with NaHCO3, brine, dried over Na2SO4, filtered and evaporated to give the title compound as a off white solid (18.52 g, 87%). 1H NMR (400 MHz, DMSO-d6) δ 0.79 (t, J=7.6 Hz, 3H), 1.20 (s, 6H), 1.38 (m, 2H), 3.01 (q, J=6.5 Hz, 2H), 4.05 (s, 2H), 6.92 (d, J=8.4 Hz, 1H), 7.13 (d, J=8.4 Hz, 1H), 7.24 (s, 2H), 7.53 (t, J=8.4 Hz, 1H), 7.55 (t, J=5.6 Hz, 1H), 9.42 (s, 1H). MS 355 (MH+).

Workup

  1. washwashed successively with NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-8e99bf6d13c443dead1493d4387b5177
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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