Water → HCID 178475875, compound

HRID 989555Notes

Reaction equation

HRID 989555 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH:19]=[O:20])(=[O:11])=[O:10])#[N:2].[N+]([O-])(O)=[O:26].[NH2:29][NH:30][C:31]([NH2:33])=[NH:32].O>C(O)C>[C:19]([OH:20])(=[O:26])[CH3:18].[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH2:19][NH:29][NH:30][C:31]([NH2:33])=[NH:32])(=[O:11])=[O:10])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 227224093-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propionaldehydeHCID 178513186HCID 178513186, compound

Product 1

HCID 178475875HCID 178475875, compoundYield 151%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[2-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]ethyl-1-methylene]ydrazinecarboximidamide hydrochloride: A solution of 3-[3-(2-cyanophenylsulfonyloxy)-5-methylphenoxy]propionaldehyde (240 mg, 0.7 mmol), as prepared in the preceding step, and aminoguanidine nitrate (200 mg, 1.5 mmol) in ethanol (8 mL) was stirred at ambient temperature overnight. Water (20 mL) was added to the reaction mixture. The precipitates were collected, washed with water (2×15 mL) and diethyl ether (2×20 mL), and dried under high vacuum. The solid was suspended in water (40 mL), treated with 2N sodium hydroxide (1.0 mL), and extracted into dichloromethane (3×50 mL). The organic phase was dried over K2CO3. After removing the solvent, the residue was dissolved in dichloromethane (1 mL), and the dichloromethane solution was added to the solution of 1.5 mL of 0.6M HCl methanol in diethyl ether (50 mL) to give the title compound as a colorless solid (245 mg, 80%). 1H-NMR (300 MHz, DMSO-d6) δ 8.28 (m, 1H), 8.09 (m, 1H), 7.97-8.04 (m, 2H), 7.55 (br s, 5 H), 6.80 (s, 1H), 6.50 (s, 2H), 4.15 (t, J=6.3 Hz, 2H), 2.68 (m, 2H), 2.22 (s, 3H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C18H19N5O4S: 402.1 (M+H), 424.1 (M+Na), 440.1 (M+K). Found: 402.1, 424.1, 440.1.

Workup

  1. customThe precipitates were collected
  2. washwashed with water (2×15 mL) and diethyl ether (2×20 mL)
  3. customdried under high vacuum
  4. additiontreated with 2N sodium hydroxide (1.0 mL)
  5. extractionextracted into dichloromethane (3×50 mL)
  6. dry with materialThe organic phase was dried over K2CO3
  7. customAfter removing the solvent
  8. dissolutionthe residue was dissolved in dichloromethane (1 mL)
  9. additionthe dichloromethane solution was added to the solution of 1.5 mL of 0.6M HCl methanol in diethyl ether (50 mL)

Sources & evidence

ORD record
ord-bd7deb81a8d7405d8840c1311b503abd
Source dataset
uspto-grants-2003_10
Patent number
US06638931B1

Reaction notes

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