Formaldehyde → HCID 13595971, compound

HRID 889533Notes

Reaction equation

HRID 889533 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3]([NH2:5])=[O:4].[CH2:8]=[O:9]>ClCCl.[OH-].[Na+]>[OH:9][CH2:8][NH:5][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 12957Trimethylacetamide

Product 1

HCID 13595971HCID 13595971, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,2-dimethylpropanamide (5.0 g, 49.4 mmol, 1.0 equiv) and aqueous sodium hydroxide (1 M, 0.494 mL, 0.494 mmol, 0.01 equiv), add aqueous formaldehyde (13.31 M, 3.71 mL, 49.4 mmol, 1.0 equiv). Stir at room temperature for 2 h, and concentrate under reduced pressure to give a white solid. Dilute the crude material with dichloromethane, dry over MgSO4, filter, and concentrate under reduced pressure to give the title compound as a white solid (6.4 g, 99%). 1H NMR (DMSO-d6, 400 MHz): δ 8.14 (br s, 1H), 5.40 (t, 1H, J=6.7 Hz), 4.46 (app t, 2H, J=6.6 Hz), 1.06 (s, 9H).

Workup

  1. concentrationconcentrate under reduced pressure
  2. customto give a white solid
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-8e48ef0446e6426296dc2c025b269e31
Source dataset
uspto-grants-2012_08
Patent number
US08252831B2

Reaction notes

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