Potassium Nitrate → HCID 19027057, compound

HRID 465316Notes

Reaction equation

HRID 465316 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[C:6]([NH:13][C:14]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:29])(=[O:26])=[O:25])=[C:20]2[C:15]=1[CH2:16][CH2:17][CH2:18][CH2:19]2)([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:7]>S(=O)(=O)(O)O>[C:6]([NH:13][C:14]1[C:23]([N+:1]([O-:4])=[O:2])=[CH:22][C:21]([S:24]([NH:27][C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:29])(=[O:26])=[O:25])=[C:20]2[C:15]=1[CH2:16][CH2:17][CH2:18][CH2:19]2)([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:7]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 19027048HCID 19027048, compound

Product 1

HCID 19027057HCID 19027057, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Potassium nitrate (0.24 g, 2.3 mmol) was added to a solution of 5-ethoxalylamino-8-ethoxalylaminosulfonyl-1,2,3,4-tetrahydronaphthalene (1.0 g, 2.3 mmol) in 12 ml of conc. sulfuric acid with stirring at 0° C. Stirring was continued for 2 h at this temperature, and then the mixture was poured into 75 ml of ice-water. The separated product was isolated by suction and washed repeatedly with water to give 0.64 g (58%) of sufficiently pure title compound. M.p. 140°-142° C. (ethanol); 1H-NMR (DMSO-d6): 1.20 (t,J=7Hz, 3H, CH3), 1.30 (t,J=7Hz, 3H, CH3), 1.58-1.90 (m, 4H, 2CH2), 2.60-2.90 (m, 2H, CH2), 3.05-3.33 (m, 2H, CH2), 3.95-4.60 (m, 4H, 2CH2), 8.27 (s, 1H, ArH), 10.9 (broad s, 1H, NH, only one exchangeable proton could be seen).

Workup

  1. stirringStirring
  2. customThe separated product was isolated by suction
  3. washwashed repeatedly with water

Sources & evidence

ORD record
ord-8355dc1bcaaf4cdd8721b4e42ce71b8d
Source dataset
uspto-grants-1992_10
Patent number
US05153195

Reaction notes

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