Formaldehyde → HCID 58342061, compound

HRID 339546Notes

Reaction equation

HRID 339546 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:10][CH:9]=1)=[O:6].[CH2:27]=O.C[O-].[Na+].[BH4-].[Na+].[OH-].[Na+]>CO>[CH3:27][NH:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:10][CH:9]=1)=[O:6]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10361109HCID 10361109, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 58342061HCID 58342061, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred mixture of 3-amino-N-[4-(6-methylbenzothiazol-2-yl)-phenyl]-benzamide (0.50 g, 1.39 mmol) and paraformaldehyde (0.059 g, 1.95 mmol) in MeOH (15 ml) at 0° C. was added dropwise a solution of sodium methoxide in MeOH (0.5 M, 3.9 ml, 1.95 mmol). The reaction mixture was then heated under reflux for 1 h. The reaction mixture was cooled to room temperature, sodium borohydride (0.081 g, 2.09 mmol) was added and heating was continued under reflux for 1 h. The reaction mixture was cooled to 0° C. amd 1 M NaOH solution (10 ml) was added, followed by extraction with DCM (3×70 ml). The combined organic extracts were dried (Na2SO4) and the solvent removed under reduced pressure to give an almost colourless solid. This was purified by flash chromatography (1:1 Hexane/EtOAc) to give the title compound (0.096 g, 18%) as a colourless solid.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 1 h
  3. temperatureheating
  4. temperatureunder reflux for 1 h
  5. additionwas added
  6. extractionfollowed by extraction with DCM (3×70 ml)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. customthe solvent removed under reduced pressure
  9. customto give an almost colourless solid
  10. customThis was purified by flash chromatography (1:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-77999809f78548f18e7c8787d2aef0af
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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