Potassium Carbonate → HCID 22706825, compound

HRID 353007Notes

Reaction equation

HRID 353007 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Cl[CH2:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH2:18])=[CH:15][CH:14]=1.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH:17]([C:16]1[CH:19]=[CH:20][C:13]([CH2:12][N:3]2[C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=[C:2]2[CH3:1])=[CH:14][CH:15]=1)=[CH2:18]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 119842-MethylbenzimidazoleHCID 14797Potassium HydroxideHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 22706825HCID 22706825, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

This Example illustrates the synthesis of polymeric blocked developer PBD1. First, 1-(4-vinylbenzyl)-2-methylbenzimidazole was prepared. A suspension of 2-methylbenzimidazole (25.0 g, 0.19 mol), 4-chloromethylstyrene (31.8 g, 0.21 mol), powdered potassium hydroxide (10.6 g, 0.19 mol), and potassium carbonate (13.1 g, 0.1 mol) in 200 mL of dry tetrahydrofuran was stirred at 25° C. for 5 d. The reaction mixture was filtered, and the solid residue extracted with additional tetrahydrofuran. The combined liquids were concentrated at reduced pressure, and the resulting brown oil was triturated with ligroin and held at −15° C. for a few hours to induce crystallization. The ligroin was decanted from the product, which was then purified by recrystallization from 70% methanol/30% water. A cream colored solid product (43.2 g, 92%) was obtained after drying. 1H NMR (CDCl3) δ 2.61 (s, 3H), 5.28 (d, J=11.0, 1H), 5.33 (s, 2H), 5.75 (d, J=17.6, 1H), 6.7 (m, 1H), 7.05 (d, J=8.1, 2H), 7.25 (m, 2H), 7.37 (d, J=8.2, 2H), 7.78 (d, J=7.3, 1H). Electrospray mass spectrometry (ES-MS) m/e 249+ (M+1).

Workup

  1. customthe synthesis
  2. filtrationThe reaction mixture was filtered
  3. extractionthe solid residue extracted with additional tetrahydrofuran
  4. concentrationThe combined liquids were concentrated at reduced pressure
  5. customthe resulting brown oil was triturated with ligroin
  6. waitheld at −15° C. for a few hours
  7. customcrystallization
  8. customThe ligroin was decanted from the product, which
  9. customwas then purified by recrystallization from 70% methanol/30% water
  10. customwas obtained
  11. customafter drying

Sources & evidence

ORD record
ord-f099c5eff99a411c981428b0209f39db
Source dataset
uspto-grants-2004_06
Patent number
US06749977B1

Reaction notes

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