Chlorosulfamic acid → HCID 86730127, compound

HRID 2205571Notes

Reaction equation

HRID 2205571 reaction equation
[NH2:1][C:2]1[C:3]([C:22]#[N:23])=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][CH2:6][C:7]([NH:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)([CH3:9])[CH3:8].[S:24](Cl)(=[O:27])(=[O:26])[NH2:25].C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[C:22]([C:3]1[C:2]([NH:1][S:24](=[O:27])(=[O:26])[NH2:25])=[CH:21][CH:20]=[CH:19][C:4]=1[O:5][CH2:6][C:7]([NH:10][C:11](=[O:18])[C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)([CH3:9])[CH3:8])#[N:23]

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 516892Sodium BicarbonateHCID 867301281622458-78-9

Product 1

HCID 86730127HCID 86730127, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-(1-(3-amino-2-cyanophenoxy)-2-methylpropan-2-yl)isonicotinamide (10.76 g, 34.67 mmol) in DMA (35 mL) was added sulfamoyl chloride (7.98 g, 69.34 mmol) at room temperature under nitrogen. The reaction mixture was then stirred at room temperature under nitrogen overnight. The resulting solution was poured into 200 mL of ice cooled NaHCO3 aqueous and stirred for 30 minutes, the precipitate was collected by filtration, after dry obtained 12.2 g of clean product as an off white solid in 90% yield. 1H NMR (400 MHz, DMSO-d6) δ 1.47 (s, 6H), 4.32 (s, 2H), 6.93 (d, J=8.8 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 7.23 (s, 2H), 7.53 (t, J=8.8 Hz, 1H), 7.67 (d, J=6 Hz, 2H), 8.29 (s, 1H), 8.66 (d, J=6.4 Hz, 2H), 9.45 (s, 1H). MS 390 (MH+).

Workup

  1. stirringstirred for 30 minutes
  2. filtrationthe precipitate was collected by filtration
  3. customafter dry

Sources & evidence

ORD record
ord-ce320472ba6444a7a5b559f5403b8d03
Source dataset
uspto-grants-2016_06
Patent number
US09371317B2

Reaction notes

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