Diethyl Ether → HCID 70543458, compound

HRID 1759252Notes

Reaction equation

HRID 1759252 reaction equation
[C:1]1([S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([C:16]1[CH:35]=[CH:34][C:19]([CH2:20][O:21][C:22]2[C:23]([CH2:28][C:29]3[NH:30][CH:31]=[CH:32][N:33]=3)=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=1)(O)=O.C(N(CC)CC)C.C(OCC)C>O1CCCC1>[NH:30]1[CH:31]=[CH:32][N:33]=[C:29]1[CH2:28][C:23]1[C:22]([O:21][CH2:20][C:19]2[CH:34]=[CH:35][C:16]([C:11](=[O:12])[NH:10][S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:8])=[O:9])=[CH:17][CH:18]=2)=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 76096Phenylsulphonyl isocyanateHCID 70543093HCID 70543093, compound

Product 1

HCID 70543458HCID 70543458, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl sulphonyl isocyanate (1.2 g) was added to a suspension of 3-(4-carboxybenzyloxy) 2-(1-imidazolylmethyl)pyridine (1.0 g) in dry tetrahydrofuran (40 ml) containing triethylamine (0.33 g). The mixture was stirred at room temperature for 8 hours and allowed to stand at room temperature for a further 36 hours. The solvents were evaporated under vacuum and aqueous 5% sodium bicarbonate solution (100 ml) added to the residue. The mixture was extracted with dichloromethane (3×50 ml) and the combined organic extracts dried, filtered and evaporated to yield an oil which solidified on trituration with diethyl ether. Recrystallization from aqueous methanol gave 2-(1-imidazolylmethyl)-3-[4-(N-phenylsulphonylcarbamoyl)benzyloxy]pyridine (0.38 g), m.p. above 250° C. Found: C, 61.47; H, 4.40; N, 12.63. C23H20N4O4S requires: C, 61.59; H, 4.50; N, 12.49%.

Workup

  1. waitto stand at room temperature for a further 36 hours
  2. customThe solvents were evaporated under vacuum and aqueous 5% sodium bicarbonate solution (100 ml)
  3. additionadded to the residue
  4. extractionThe mixture was extracted with dichloromethane (3×50 ml)
  5. customthe combined organic extracts dried
  6. filtrationfiltered
  7. customevaporated
  8. customto yield an oil which
  9. customRecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-a3b09942bcdb4c10a860a102600a8e7a
Source dataset
uspto-grants-1982_07
Patent number
US04339583

Reaction notes

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