Formaldehyde → Benzotriazol-1-ylmethyl-(2-thiophen-2-yl-ethyl)-amine

HRID 1676506Notes

Reaction equation

HRID 1676506 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][CH2:16][NH2:17].[CH2:18]=O>CCOCC>[N:1]1([CH2:18][NH:17][CH2:16][CH2:15][C:11]2[S:10][CH:14]=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 116521ThiopheneethanamineHCID 178418385HCID 178418385, compound

Product 1

HCID 86637495Benzotriazol-1-ylmethyl-(2-thiophen-2-yl-ethyl)-amineYield 100.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 12 g (0.1 mole) benzotriazole and 13 g (0.1 mole) of 2-thiophen-2-yl-ethylamine in 500 mL of ether was added dropwise 7.4 mL (0.1 mole) of 37% aqueous formaldehyde. The reaction mixture was stirred at room temperature overnight. The solution was dried over calcium chloride, filtered and concentrated under pressure. Hexane was added to the residue cooled in an ice bath and the resulting solid was collected by filtration, washing with hexane and then dried to give 26.0 g of benzotriazol-1-ylmethyl-(2-thiophen-2-yl-ethyl)-amine as a light yellow oil (100%).

Workup

  1. dry with materialThe solution was dried over calcium chloride
  2. filtrationfiltered
  3. concentrationconcentrated under pressure
  4. additionHexane was added to the residue
  5. temperaturecooled in an ice bath
  6. filtrationthe resulting solid was collected by filtration
  7. washwashing with hexane
  8. customdried

Sources & evidence

ORD record
ord-dd856bbe421f422e85ec2134d5f4d93d
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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