Formaldehyde → HCID 9835167, compound

HRID 2276906Notes

Reaction equation

HRID 2276906 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[CH2:19]=O.C[O-].[Na+].[BH4-].[Na+]>CO>[CH3:19][NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 4311764Sodium borohydrideHCID 10942334Sodium Methoxide

Product 1

HCID 9835167HCID 9835167, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-(4-Aminophenyl)-6-methoxybenzothiazole (43, 779 mg, 3.04 mmol) and paraformaldehyde (487 mg, 15.2 mmol) were dissolved in methanol and then added to 0.5 M NaOMe in methanol (30 mL, 15.2 mmol). The resulting reaction mixture was agitated for 4 hours at room temperature and, after adding NaBH4 (1.0 g, 26.5 mmol), heated for 1.5 hours under reflux. After removing methanol by distilling under reduced pressure, the residue was dissolved in ethyl acetate (100 mL) and water was added thereto. After extracting the organic compound with ethyl acetate, removing water using sodium sulfate and removing the solvent under reduced pressure, column chromatography yielded the target compound 2-[4-(N-monomethyl)aminophenyl)-6-methoxybenzothiazole (44, 588 mg, 72%) as yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated for 1.5 hours
  3. temperatureunder reflux
  4. customAfter removing methanol
  5. distillationby distilling under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  7. additionwater was added
  8. extractionAfter extracting the organic compound with ethyl acetate
  9. customremoving water
  10. customremoving the solvent under reduced pressure, column chromatography

Sources & evidence

ORD record
ord-51228633fcd84afba7a565a6433752e1
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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