Formaldehyde → HCID 57595175, compound

HRID 1785401Notes

Reaction equation

HRID 1785401 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH:16]=[O:17])[CH:13]=[CH:12][N:11]3[C:18]=2[C:19]2[CH:24]=[CH:23][N:22]=[C:21]([S:25][CH3:26])[N:20]=2)=[CH:4][CH:3]=1.[NH:27]([CH2:29]C(O)=O)[CH3:28].[CH2:33]=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH:16]4[O:17][CH2:33][N:27]([CH3:29])[CH2:28]4)[CH:13]=[CH:12][N:11]3[C:18]=2[C:19]2[CH:24]=[CH:23][N:22]=[C:21]([S:25][CH3:26])[N:20]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1088SarcosineHCID 57595184HCID 57595184, compound

Product 1

HCID 57595175HCID 57595175, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 250 mL round bottom flask equipped with a Dean Stark trap was charged with aldehyde 40 (1.44 g, 3.95 mmol), toluene (120 mL), sarcosine (710 mg, 7.97 mmol), and paraformaldehyde (600 mg, 20.0 mmol), and the reaction was heated under reflux for 12 hours, then concentrated under reduced pressure, dissolved in a minimum volume of acetone, and filtered through a 5 g silica cartridge, which was then washed with 80 mL of acetone. The filtrate was then concentrated under reduced pressure, and not purified further. Yield of 41: 1.65 g (98%). 1H NMR (400 MHz, CDCl3) δ 2.63 (bs, 6H), 2.94 (m, 1H), 3.55 (m, 1H), 4.65 (m, 1H), 4.69 (m, 1H), 5.18 (m, 1H), 6.80 (d, J=5.4 Hz, 1H), 6.97 (d, J=7.6 Hz, 1H), 7.13 (t, J=8.4 Hz, 2H), 7.61 (m, 2H), 7.69 (s, 1H), 8.29 (d, J=5.4 Hz, 1H), 9.56 (d, J=7.6 Hz, 1H). MS (ESI+) 410.2 (under MS conditions, the aminal bond is cleaved and instead an M+1 peak is observed for the resulting 7-C(OH)HCH2N(Me)H product).

Workup

  1. customA 250 mL round bottom flask equipped with a Dean Stark trap
  2. temperaturethe reaction was heated
  3. temperatureunder reflux for 12 hours
  4. concentrationconcentrated under reduced pressure
  5. dissolutiondissolved in a minimum volume of acetone
  6. filtrationfiltered through a 5 g silica cartridge, which
  7. washwas then washed with 80 mL of acetone
  8. concentrationThe filtrate was then concentrated under reduced pressure
  9. customnot purified further

Sources & evidence

ORD record
ord-efcc27b145fc4b6dbfe3817357eba0c9
Source dataset
uspto-grants-2009_03
Patent number
US07504501B2

Reaction notes

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