Hydrochloric Acid → HCID 86698208, compound

HRID 76323Notes

Reaction equation

HRID 76323 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C=O.Cl.O.[Cl:24][CH2:25]Cl>>[Cl:24][CH2:25][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:11][CH2:12][NH:13][C:14](=[O:19])[C:15]([F:17])([F:18])[F:16]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 962WaterHCID 6344DichloromethaneHCID 592128Acetamide, N-(2-(3,4-dimethoxyphenyl)ethyl)-2,2,2-trifluoro-

Product 1

HCID 86698208HCID 86698208, compoundYield 77%

Procedure

In a three-necked flask, mix N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide (35 g, 126 mmoles) and 37% aqueous formaldehyde (776 mL, 1.014 mole) in 120 mL of dichloromethane at 0° C. To the resulting two-phase mixture slowly add, at 0° C., 345 mL of 37% aqueous hydrochloric acid solution and heat at 40° C. After being in contact for 3 hours, hydrolyse the mixture using 250 mL of water and wash the aqueous phase with dichloromethane (2×100 mL). Combine the organic phases, dry them over MgSO4 and carry out drying in vacuo to obtain a beige meringue (38.2 g). The product obtained is recrystallised from toluene to obtain 31.5 g of a white powder corresponding to the title compound.

Workup

  1. additionTo the resulting two-phase mixture slowly add, at 0° C.
  2. washwash the aqueous phase with dichloromethane (2×100 mL)
  3. dry with materialCombine the organic phases, dry them over MgSO4
  4. customcarry out drying in vacuo
  5. customto obtain a beige meringue (38.2 g)
  6. customThe product obtained
  7. customis recrystallised from toluene

Sources & evidence

ORD record
ord-57d07fd870314cf782381a670bba7ba1
Source dataset
uspto-grants-2014_09
Patent number
US08835627B2

Reaction notes

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