Formaldehyde → HCID 10468315, compound

HRID 2116586Notes

Reaction equation

HRID 2116586 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, 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-f5b5c4351c3e4bb983b7efb651690289
Source dataset
uspto-grants-2008_10
Patent number
US07439251B2

Reaction notes

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