Sodium Hydroxide → HCID 66746636, compound

HRID 1467188Notes

Reaction equation

HRID 1467188 reaction equation
[S:1]([NH:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH2:16][CH3:17])[C:7]=1[C:8]#[N:9])(=[O:4])(=[O:3])[NH2:2].[OH-].[Na+]>C(O)C>[NH2:9][C:8]1[C:7]2[C:10]([O:14][CH2:15][CH2:16][CH3:17])=[CH:11][CH:12]=[CH:13][C:6]=2[NH:5][S:1](=[O:4])(=[O:3])[N:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66745932HCID 66745932, compound

Product 1

HCID 66746636HCID 66746636, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-sulfamoylamino-6-propoxybenzonitrile (Example 158a) (4.73 g, 18.53 mmol) in ethanol (65 mL), was added aqueous NaOH (2N, 18.6 ml, 37.06 mmol). The resulting clear solution was refluxed for 3 hours under nitrogen. After cooling to room temperature, the resulting solution was filtered, the filtrate was cooled to 0° C. and neutralized with 10% acetic acid. The resulting precipitate was collected by filtration, suspended in 50 ml of ethanol/water (1:1) and warmed to 40° C. for 20 min. The solid was collected by filtration to provide 4-Amino-5-(propyloxy)-1H-benzo[c][1,2,6]thiadiazine-2,2-dioxide (4 g, 85%) as a pale yellow powder. M.p.: 229-230° C. 1H NMR (400 MHz, DMSO-d6) δ 0.96 (t, J=7.3 Hz, 3H), 1.81 (sext, J=7.3 Hz, 2H), 4.10 (t, J=6.7 Hz, 2H), 6.60 (d, J=8.6 Hz, 1H), 6.73 (d, J=8.6 Hz, 1H), 7.44 (t, J=8.6 Hz, 1H), 7.81 (br s, 1H), 8.35 (br s, 1H), 10.93 (br s, 1H). 13C NMR (400 MHz, DMSO-d6) δ 11.07, 22.18, 71.41, 100.93, 105.64, 110.21, 135.53, 145.16, 158.47, 161.10. MS 256 (MH+).

Workup

  1. temperatureThe resulting clear solution was refluxed for 3 hours under nitrogen
  2. filtrationthe resulting solution was filtered
  3. temperaturethe filtrate was cooled to 0° C. and neutralized with 10% acetic acid
  4. filtrationThe resulting precipitate was collected by filtration
  5. temperaturewarmed to 40° C. for 20 min
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-31f0d83ab1ba4023bfe684fabfb92c6e
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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