Dimethylformamide → HCID 178433217, compound

HRID 1708940Notes

Reaction equation

HRID 1708940 reaction equation
CN(C=O)C.S(Cl)(Cl)=O.[NH:10]1[C:14]([C:15]([OH:17])=O)=[N:13][N:12]=[N:11]1.[CH3:18][C:19]1[S:20][CH:21]=[C:22]([NH2:24])[N:23]=1>C(#N)C.N1C=CC=CC=1.O.C1C=CC=CC=1>[CH3:18][C:19]1[S:20][CH:21]=[C:22]([NH:24][C:15]([C:14]2[NH:13][N:12]=[N:11][N:10]=2)=[O:17])[N:23]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 147727002-Methyl-1,3-thiazol-4-amineHCID 178524966HCID 178524966, compound

Product 1

HCID 178433217HCID 178433217, compoundYield 41.1%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 6342AcetonitrileSolvent2×

Procedure

A mixture, obtained by adding dry DMF(0.43 ml, 5.55 mmol) and then thionyl chloride (0.405 ml, 5.55 mmol) to dry benzene (1 ml) under ice-cooling, was allowed to warm up to room temperature and to react for 10 minutes upon which the mixture separated into two layers. The lower layer was added dropwise to dipotassium salt of 1H-tetrazole-5-carboxylic acid (704 mg, 3.70 mmol) suspended in dry acetonitrile (9 ml) under ice-cooling, and the mixture was allowed to react for 15 minutes. After adding dropwise a mixed solution of 2-methyl-4-thiazolamine (447.8 mg, 3.92 mmol) in dry acetonitrile (5 ml) and dry pyridine (1 ml) under the same conditions, the mixture was allowed to warm up to room temperature and to react for 1 hour. To the reaction mixture was added water, and the insoluble solids was removed by filtration and the filtrate was acidified with ice-cooled 2N HCl to pH 2. The precipitates were filtered, washed with water, and recrystallized from DMF-water to give yellowish crystals (320 mg, yield 41%) of N-(2-methyl-4-thiazolyl)-1H-tetrazole-5-carboxamide (Ia-1), m.p. 295°-297° C. (decomp).

Workup

  1. customA mixture, obtained
  2. customto react for 10 minutes upon which the mixture
  3. customseparated into two layers
  4. temperaturecooling
  5. customto react for 15 minutes
  6. temperatureto warm up to room temperature
  7. customto react for 1 hour
  8. customthe insoluble solids was removed by filtration
  9. temperaturecooled 2N HCl to pH 2
  10. filtrationThe precipitates were filtered
  11. washwashed with water
  12. customrecrystallized from DMF-water

Sources & evidence

ORD record
ord-e7e64689e0ab4069ab351ff678b63b39
Source dataset
uspto-grants-1990_08
Patent number
US04946855

Reaction notes

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