Formaldehyde → HCID 18630142, compound

HRID 725560Notes

Reaction equation

HRID 725560 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[C:6]([CH:12]=1)[C:7]([NH:9][CH2:10][CH3:11])=[O:8].[NH:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1.[CH2:26]=O>C(O)C>[N:17]1([CH2:26][NH:1][C:2]2[CH:3]=[CH:4][C:5]([Si:13]([CH3:15])([CH3:14])[CH3:16])=[C:6]([CH:12]=2)[C:7]([NH:9][CH2:10][CH3:11])=[O:8])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 18630262HCID 18630262, compoundHCID 178418385HCID 178418385, compound

Product 1

HCID 18630142HCID 18630142, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound of Example 217 (0.29 g, 1.2 mmol) and benzotriazole (0.143 g, 1.2 mmol) in absolute ethanol (5 mL) at RT was added 37% aq formaldehyde (0.090 mL, 1.2 mmol). An aliquot was induced to precipitate by cooling and addition of a small amount of water. The precipitate was added back into the reaction which was stirred at RT overnight and cooled in a refrigerator for 6 h. The resultant mixture was filtered and dried under vacuum (P2O5) to afford 5-[(1H-benzotriazol-1-ylmethyl)amino]-N-ethyl-2-(trimethylsilyl)benzamide as a white solid (0.308 g, 70%). m.p. 207°-208° C.

Workup

  1. customto precipitate
  2. temperatureby cooling
  3. additionaddition of a small amount of water
  4. additionThe precipitate was added back into the reaction which
  5. temperaturecooled in a refrigerator for 6 h
  6. filtrationThe resultant mixture was filtered
  7. dry with materialdried under vacuum (P2O5)

Sources & evidence

ORD record
ord-f28e050df7754bbeb98fd1f9aad092cf
Source dataset
uspto-grants-1998_01
Patent number
US05705513

Reaction notes

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