Guanidine Hydrochloride → HCID 136068845, compound

HRID 1073774Notes

Reaction equation

HRID 1073774 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[O-]CC.[Na+].[C:10]([CH:12]([C:28](OCC)=[O:29])[CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1)#[N:11]>C(O)C>[NH2:4][C:3]1[NH:5][C:28](=[O:29])[C:12]([CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=2)=[C:10]([NH2:11])[N:2]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 2723922Sodium ethoxideHCID 14858818HCID 14858818, compound

Product 1

HCID 136068845HCID 136068845, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Guanidine hydrochloride (4.18 g, 43.7 mmoles) was added to a solution of sodium ethoxide (65.6 mmoles) in ethanol (25 mL), and the mixture was treated with compound 1A (7.0 g, 21.9 mmoles) as a solution in ethanol (25 mL) and then refluxed for 7 hours. After cooling, the mixture was filtered, the solid residue was washed with 3 volumes (10 mL) of ethanol, and the combined filtrate and washings were treated with acetic acid to pH ~ 7.0. The filtrate was evaporated in vacuo to a viscous residue and treated with water (50 mL). Filtration gave a solid, which was washed with 3 volumes (10 mL) of water and dried at 50° C. in vacuo to give 6.76 g (93%) of compound 1B as a white solid. NMR (DMSO-d6) δ 1.28 (t, 3H, CH3 of ester), 1.75 (m, 2H, CH2 --CH2 -- CH2), 2.25 (t, 2H, CH2 --CH2CH2 --O), 3.97 (t, 2H, --CH2 --O), 4.25 (q, 2H, CH2 of ester), 5.7 (s, 2H, NH2), 5.93 (s, 2H, NH2), 6.98 (d, 2H, benzoate H's ortho to oxygen), 7.85 (d, 2H, benzoate H's ortho to carbonyl), 9.8 (br s, 1H, ring NH). The intermediate, compound 1B, was used in the next reaction without further purification.

Workup

  1. temperaturerefluxed for 7 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. washthe solid residue was washed with 3 volumes (10 mL) of ethanol
  5. additionthe combined filtrate and washings were treated with acetic acid to pH ~ 7.0
  6. customThe filtrate was evaporated in vacuo to a viscous residue
  7. additiontreated with water (50 mL)
  8. filtrationFiltration
  9. customgave a solid, which
  10. washwas washed with 3 volumes (10 mL) of water
  11. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-c1e46fb979d04165a44087db22efe638
Source dataset
uspto-grants-1990_11
Patent number
US04971973

Reaction notes

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