Sodium Hydroxide → HCID 57939018, compound

HRID 603103Notes

Reaction equation

HRID 603103 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH2:10][CH2:11][OH:12])[C:6]=2[C:13]=1[F:14].P([O-])([O-])([O-])=[O:16].[Na+].[Na+].[Na+].CC1(C)N([O])C(C)(C)CCC1.[O-]Cl=O.[Na+].[O-]Cl.[Na+].[O-]S([O-])=O.[Na+].[Na+].[OH-].[Na+]>O.CC#N>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH2:10][C:11]([OH:16])=[O:12])[C:6]=2[C:13]=1[F:14]

Participants

10

Reactant 7

HCID 14798Sodium HydroxideHCID 24243Trisodium PhosphateHCID 24437Sodium SulfiteHCID 2724126Tempo2×HCID 23665760Sodium HypochloriteHCID 23668197Sodium Chlorite2×HCID 579390212-(6,7-difluoro-1H-benzimidazol-1-yl)ethanol

Product 1

HCID 57939018HCID 57939018, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
42 °C

Procedure

2-(6,7-difluoro-1H-benzimidazol-1-yl)ethanol (2.96 g, 15 mmol) is taken into 75 ml of MeCN and sodium phosphate buffer (56 ml, 0.67 M, pH 6.8) and the mixture is heated to 42° C. TEMPO (165 mg, 1.05 mol) is added followed by the simultaneous dropwise addition of a solution of NaClO2 (3.38 g, 80% pure, 30 mmol in 15 ml water) and a solution of bleach (350 μL of 6% NaOCl in 7.5 mL water) over 1.5 hours. After 48 hrs, the same quantities of NaClO2 and bleach are added. After a further 24 hours, TEMPO (165 mg, 1.05 mol) is added and the reaction is stirred for 72 hrs. The darkened reaction is allowed to cool to room temperature followed by the dropwise addition of 30 ml of a saturated solution of Na2SO3 (exothermic). The reaction becomes almost colourless. Using 2 N NaOH, the pH is raised to 9.2 and the reaction is extracted 4 times with ethyl acetate. The pH is then lowered to 3.8 with 2 N HCl and the solution allowed to stand for 48 hours. 1.98 grams of white crystalline material is recovered. The mother liquor is reduced to half the volume and allowed to stand. A further 260 mg is collected. (Combined yield 2.23 g, 70%)

Workup

  1. waitAfter a further 24 hours
  2. customThe darkened reaction
  3. temperatureto cool to room temperature
  4. temperaturethe pH is raised to 9.2
  5. extractionthe reaction is extracted 4 times with ethyl acetate
  6. waitto stand for 48 hours
  7. custom1.98 grams of white crystalline material is recovered
  8. customA further 260 mg is collected

Sources & evidence

ORD record
ord-b91a7bb5b8a0409d8b45ed212a72c775
Source dataset
uspto-grants-2011_03
Patent number
US07906654B2

Reaction notes

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