Dimethylformamide → HCID 178423744, compound

HRID 2052674Notes

Reaction equation

HRID 2052674 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[C:5]([C:13]([OH:15])=O)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(OC(Cl)=O)C.O.N[N:24]1[N:28]=[N:27][CH:26]=[N:25]1.C[N:30](C)C=O>C(N(CC)CC)C>[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[C:5]([C:13](=[O:15])[NH:30][C:26]3[NH:25][N:24]=[N:28][N:27]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 10928Ethyl chloroformateHCID 20376339HCID 20376339, compoundHCID 203763402-Aminotetrazole monohydrate

Product 1

HCID 178423744HCID 178423744, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred ice bath-cooled solution of 4.0 g. (0.020 mole) of 2,4-dimethyl-8-quinoline carboxylic acid in 20 ml. of N,N-dimethyl formamide is added 2.8 ml. of triethyl amine. To this solution is added dropwise 2 ml. of ethylchloroformate. The mixture is stirred for one hour, then 2 g. (0.020 mole) of 2-aminotetrazole monohydrate in 10 ml. of N,N-dimethylformamide is added. The mixture is stirred at 20° C. for about 16 hours then evaporated to provide a residue which is washed with water. The residue is recrystallized twice from acetic acid to provide 2,4-dimethyl-8-(1H-tetrazole-5-ylcarbamoyl)quinoline, m.p. 300°-305° C.

Workup

  1. additionTo this solution is added dropwise 2 ml
  2. stirringThe mixture is stirred at 20° C. for about 16 hours
  3. customthen evaporated
  4. customto provide a residue which
  5. washis washed with water
  6. customThe residue is recrystallized twice from acetic acid

Sources & evidence

ORD record
ord-e0ad8117884148dfbe512037993ce3a7
Source dataset
uspto-grants-1980_01
Patent number
US04186201

Reaction notes

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