Sodium Hydroxide → HCID 22928805, compound

HRID 2064049Notes

Reaction equation

HRID 2064049 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:16][CH2:15][N:14](C(OCC)=O)[CH2:13][CH2:12]3)[C:6]=2[CH:22]=1.[OH-].[Na+]>Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 59863023HCID 59863023, compound

Product 1

HCID 22928805HCID 22928805, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

D3 (9.6 g, 30 mmol) was suspended in a 2.5M aqueous solution of sodium hydroxide (75 mL). The suspension was refluxed for 15 hours and then allowed to cool. The solution was acidified with 6M HCl (˜40 mL) until no more effervescence was observed (˜pH 2) and then the pH was carefully adjusted to pH 8.5 using 2.5 M aqueous NaOH. The resulting precipitate was collected by filtration, washed with cold water (20 mL) and then dried under vacuum at 40° C. for 15 hours to give the title compound (7.5 g, 100% yield) as a light purple solid (Rf: Baseline (ethyl acetate)). 1H-NMR (300 MHz, DMSO-d6) □ 10.98 (1H, br s), 8.93 (1H, br s), 7.40 (1H, d), 6.93 (1H, dd), 6.79 (1H, dd), 4.51-4.48 (1H, m), 3.35-3.32 (2H, m), 3.02-2.98 (2H, m), 2.55-2.52 (2H, m), 1.78-1.74 (2H, m); m.p.>190° C. (decomp).

Workup

  1. temperatureThe suspension was refluxed for 15 hours
  2. temperatureto cool
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with cold water (20 mL)
  5. customdried under vacuum at 40° C. for 15 hours

Sources & evidence

ORD record
ord-b5cf2ce0f8294547825dcb780a4e9b57
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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