Dimethylformamide → HCID 19981425, compound

HRID 1461000Notes

Reaction equation

HRID 1461000 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[N:4][N:3]=1.[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[N:22]=[C:23]=[O:24].CN(C)C=O>ClCCCl.O>[CH3:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH3:14])[C:16]=1[NH:22][C:23]([NH:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:5]=[N:4][N:3]=1)=[O:24]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 987872,6-Xylyl isocyanateHCID 56307431694-90-3

Product 1

HCID 19981425HCID 19981425, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

5-Amino-1-benzyltetrazole (3.25 g, 0.0186 mol) was suspended in 15 mL of 1,2-dichloroethane after which 2,6-dimethylphenylisocyanate (3.5 mL, 0.025 mol) was added. The mixture was refluxed for 6 hours, 10 mL of dimethylformamide was added, and the mixture was refluxed for an additional 6 hours. The reaction mixture was diluted twice with 50 mL water and the water decanted from the precipitate then concentrated in vacuo adding ethanol as the azeotropic solvent. The precipitate was washed with ether, dried in a vacuum oven, washed with hot water and hot ethyl acetate, extracted with hot 9:1 methanol/methylene chloride, and concentrated to give the title compound, m.p. 220-230° C. dec.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 6 hours
  3. temperaturethe mixture was refluxed for an additional 6 hours
  4. customthe water decanted from the precipitate
  5. concentrationthen concentrated in vacuo
  6. additionadding ethanol as the azeotropic solvent
  7. washThe precipitate was washed with ether
  8. customdried in a vacuum oven
  9. washwashed with hot water and hot ethyl acetate
  10. extractionextracted with hot 9:1 methanol/methylene chloride
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-bd7b50270dd242f3a6d872098c94abe6
Source dataset
uspto-grants-1991_12
Patent number
US05073565

Reaction notes

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