Sodium Hydroxide → HCID 67399877, compound

HRID 711910Notes

Reaction equation

HRID 711910 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:12][C:11]2([CH3:14])[CH3:13])[C:3]=1[C:4]#[N:5].[S:15](Cl)(=[O:18])(=O)[NH2:16].[OH-:20].[Na+]>CC(N(C)C)=O.O>[CH3:13][C:11]1([CH3:14])[CH2:12][CH:10]1[C:6]1[C:3]2[C:4]([NH2:5])=[N:16][S:15](=[O:18])(=[O:20])[NH:1][C:2]=2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24499Chlorosulfamic acidHCID 67400694HCID 67400694, compound

Product 1

HCID 67399877HCID 67399877, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-amino-6-(2,2-dimethylcyclopropyl)benzonitrile (381 mmol, 71 mg) (Example 270a) and sulfamoyl chloride (572 mmol, 66 mg) in DMA (1 mL) was stirred at room temperature. After 1 hour, the reaction mixture was diluted with NaOH (1N, 572 mmol, 572 μL) and water (˜30 mL). The precipitate was filtered off, washed with water (3×5 mL) then dissolved in EtOH (10 mL) and NaOH (1N, 953 μL) was added. The reaction was heated to 80° C. with stirring. After completion the solvent were evaporated and the residue was partitioned between water (20 mL) and ether (5 mL). The aqueus layer was extracted with ether (2×5 mL), then acidified to pH˜3 with 1N HCl. The precipitate was collected, washed with water, dried in vacuo to give the desired product (59 mg, 58%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 0.610 (m, 1H), 0.63 (s, 3H), 0.89 (m, 1H), 1.20 (s, 3H), 2.48 (m, 1H), 6.88 (d, J=8 Hz, 1H), 6.92 (d, J=8 Hz, 1H), 7.21 (br. s, 1H), 7.39 (t, J=8 Hz, 1H), 8.42 (br. s, 1H), 10.74 (s, 1H). MS 266 (MH+).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water (3×5 mL)
  3. dissolutionthen dissolved in EtOH (10 mL)
  4. additionNaOH (1N, 953 μL) was added
  5. customAfter completion the solvent were evaporated
  6. customthe residue was partitioned between water (20 mL) and ether (5 mL)
  7. extractionThe aqueus layer was extracted with ether (2×5 mL)
  8. customThe precipitate was collected
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-2b4e87d147684a459d18f3b1459086e6
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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