2-Furancarbonyl chloride → HCID 20544870, compound

HRID 2285528Notes

Reaction equation

HRID 2285528 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:13]=2)=[N:5][C:4]([NH2:25])=[N:3]1.[O:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](Cl)=[O:32]>N1C=CC=CC=1>[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:13]=2)=[N:5][C:4]([NH:25][C:31]([C:27]2[O:26][CH:30]=[CH:29][CH:28]=2)=[O:32])=[N:3]1

Participants

4

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 71988Lamtidine

Product 1

HCID 20544870HCID 20544870, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-methyl-N5 -[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine (A) (1.0 g) and 2-furancarboxylic acid, chloride (0.42 g) in pyridine (25 ml) was kept at ambient temperature for 1 h. The pyridine was evaporated in vacuo and the residue was azeotropically distilled with toluene to give an oil which was partitioned between ethyl acetate and 2 M hydrochloric acid. The pH of the aqueous extract was adjusted to pH 9 and it was extracted with ethyl acetate. The organic extracts were evaporated to a gum which was chromatographed on silica using ethyl acetate: methanol (9:1) to give the title compound (0.30 g) as a glassy solid. tlc System B, Rf 0.57. Nmr (CDCl3) 1.5,brs, (1H); 2.53,m, (1H); 2.75,t+m, (2H); 3.0-3.3,m, (3H); 3.5,dd (1H); 5.31,t, (1H); 5.92,t, (2H); 6.42,q, (2H); 6.50,s, (3H); 6.59,s, (3H); 7.6,brs; (4H); 7.9,m, (2H); 8.5,m, (6H).

Workup

  1. customThe pyridine was evaporated in vacuo
  2. distillationthe residue was azeotropically distilled with toluene
  3. customto give an oil which
  4. customwas partitioned between ethyl acetate and 2 M hydrochloric acid
  5. extractionThe pH of the aqueous extract
  6. extractionwas extracted with ethyl acetate
  7. customThe organic extracts were evaporated to a gum which
  8. customwas chromatographed on silica

Sources & evidence

ORD record
ord-bbbdb3cd754848209e4d467d42c8a809
Source dataset
uspto-grants-1982_04
Patent number
US04323566

Reaction notes

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