Chlorosulfamic acid → HCID 66745932, compound

HRID 1467189Notes

Reaction equation

HRID 1467189 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][CH3:13])[C:3]=1[C:4]#[N:5].[S:14](Cl)(=[O:17])(=[O:16])[NH2:15]>CC(N(C)C)=O>[S:14]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][CH3:13])[C:3]=1[C:4]#[N:5])(=[O:17])(=[O:16])[NH2:15]

Participants

4

Reactant 2

HCID 24499Chlorosulfamic acidHCID 24777776HCID 24777776, compound

Product 1

HCID 66745932HCID 66745932, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-amino-6-propoxybenzonitrile (Example 158b) (4.23 g, 24.01 mmol) in dimethylacetamide (20 mL) under N2 was added sulfamoyl chloride (5.56 g, 48.02 mmol). The reaction mixture was then stirred at room temperature under nitrogen for 4 hours. Upon completion, the reaction was quenched by addition of ice/water (250 mL). The resulting precipitate was collected by filtration, rinsed with water and dried to yield 2-sulfamoylamino-6-propoxybenzonitrile (4.73 g, 77%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 1.01 (d, J=7.2 Hz, 3H), 1.76 (sext, J=7.2 Hz, 2H), 4.08 (t, J=6.8 Hz, 2H), 6.96 (d, J=8.5 Hz, 1H), 7.15 (t, J=8.5 Hz, 1H), 7.28 (br s, 2H), 7.57 (d, J=8.5 Hz, 1H), 9.46 (s, 1H). MS 256 (MH+).

Workup

  1. customUpon completion, the reaction was quenched by addition of ice/water (250 mL)
  2. filtrationThe resulting precipitate was collected by filtration
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-c4d832f5951946eebda7d2a41596d690
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

Loading…