Dimethylformamide → HCID 118290400, compound

HRID 628487Notes

Reaction equation

HRID 628487 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[CH:11]1([C:14]2[C:15]([CH2:27][O:28][C:29]3[CH:34]=[CH:33][C:32]([N:35]4[C:39]([CH3:40])=[CH:38][C:37]([CH3:41])=[N:36]4)=[CH:31][C:30]=3[CH3:42])=[C:16]([N:20]3[C:24](=[O:25])[N:23]([CH3:26])[N:22]=[N:21]3)[CH:17]=[CH:18][CH:19]=2)[CH2:13][CH2:12]1>O>[CH:11]1([C:14]2[C:15]([CH2:27][O:28][C:29]3[CH:34]=[CH:33][C:32]([N:35]4[C:39]([CH3:40])=[C:38]([CH:3]=[O:4])[C:37]([CH3:41])=[N:36]4)=[CH:31][C:30]=3[CH3:42])=[C:16]([N:20]3[C:24](=[O:25])[N:23]([CH3:26])[N:22]=[N:21]3)[CH:17]=[CH:18][CH:19]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 118290431HCID 118290431, compound2×

Product 1

HCID 118290400HCID 118290400, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, a mixture of N,N-dimethylformamide 20 ml and phosphorus oxychloride 0.85 ml was stirred for one hour. To the above-mentioned mixture was added 1-{3-cyclopropyl-2-[2-methyl-4-(3,5-dimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (Present compound 3) 2.0 g and was stirred at 100° C. for three hours. At room temperature, to the resulting mixture was added water 10 ml. The mixture was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-{3-cyclopropyl-2-[2-methyl-4-(3,5-dimethyl-4-formyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter, referred to as “Present compound 51”) 1.7 g.

Workup

  1. stirringwas stirred at 100° C. for three hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-53f1e099531743e295ea3999a968717d
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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