Formaldehyde → HCID 10468315, compound

HRID 1825848Notes

Reaction equation

HRID 1825848 reaction equation
[CH3:1][N:2]1[CH2:12][CH2:11][C:5]2([S:9][CH2:8][C:7](=[O:10])[NH:6]2)[CH2:4][CH2:3]1.C=O.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[C:20]1(C)C=CC=CC=1>C(O)C>[CH3:1][N:2]1[CH2:12][CH2:11][C:5]2([S:9][CH2:8][C:7](=[O:10])[N:6]2[CH2:20][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1140TolueneHCID 31268PyrrolidineHCID 22139638HCID 22139638, compound

Product 1

HCID 10468315HCID 10468315, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 8-Methyl-1-thia-4,8-diaza-spiro[4.5]decan-3-one (AF277 5.13 g, 0.0275 mol), formaldehyde (37% solution, 2.75 ml), and pyrrolidine (2.3 ml, 0.0275 mole) in ethanol (2.3 ml) was refluxed for 4 h, then left at room temperature over night. Toluene (10 ml) was added and the solvent was evaporated. Boiling pentane (100 ml) was added to the residue and the solution was decanted. The trituration with hot pentane was repeated four times, the pentane layers were combined, cooled to 0° C. and the precipitate was collected and identified as AF287 (4.6 gr, 63% yield). 1H-NMR (CDCl3) δ 1.69–1.77 (m, 5H), 2.20–2.29 (s and m, 5H, CH3, and CH2), 2.43–2.58 (m, 6H), 2.82–2.86 (m, 2H), 3.50 (s, 2H), 3.50 (s, 2H, SCH2), 4.14 (s, 2H, NCH2N) ppm. MS (EI) m/e 269(M+); 198; 84; 70.

Workup

  1. waitleft at room temperature over night
  2. customthe solvent was evaporated
  3. additionBoiling pentane (100 ml) was added to the residue
  4. customthe solution was decanted
  5. customthe precipitate was collected

Sources & evidence

ORD record
ord-0216e500e04b43a886c442c96560293b
Source dataset
uspto-grants-2006_05
Patent number
US07049321B2

Reaction notes

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