Thionyl Chloride → HCID 178488847, compound

HRID 354790Notes

Reaction equation

HRID 354790 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]=1[N:15]=[C:14]1[C:9]([CH:10]=[CH:11][CH:12]=[C:13]1[C:17]([OH:19])=O)=[N:8]2.O.[NH2:21][C:22]1[NH:26][N:25]=[N:24][N:23]=1.S(Cl)(Cl)=O>N1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]=1[N:15]=[C:14]1[C:9]([CH:10]=[CH:11][CH:12]=[C:13]1[C:17]([NH:21][C:22]1[NH:26][N:25]=[N:24][N:23]=1)=[O:19])=[N:8]2

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 12318573HCID 12318573, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178488847HCID 178488847, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 0.006 mole (1.5 g) of 9-methoxyphenazine-1-carboxylic acid and 0.006 mole (0.61 g) of 5-aminotetrazole monohydrate in 50 ml of pyridine was added dropwise 0.012 mole (1.4 g) of thionyl chloride. The mixture was warmed to 70° C., maintained at 70° C. for 20 minutes, then diluted with water. A solid product was separated from the mixture by filtration, washed with water and acetone, and dried. Recrystallization from N,N-dimethylformamide provided 9-methoxy-(N-tetrazol-5-yl)phenazine-1-carboxamide, in the form of orange needles, m.p. 325°-330° C. (dec.)

Workup

  1. temperaturemaintained at 70° C. for 20 minutes
  2. customA solid product was separated from the mixture by filtration
  3. washwashed with water and acetone
  4. customdried
  5. customRecrystallization from N,N-dimethylformamide

Sources & evidence

ORD record
ord-0f6c70edb1c148beb54c331549a5b114
Source dataset
uspto-grants-1983_03
Patent number
US04377579

Reaction notes

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