Hydrochloric Acid → HCID 178522473, compound

HRID 1708942Notes

Reaction equation

HRID 1708942 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.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[S:25][CH:26]=[C:27]([NH2:29])[N:28]=2)[CH:19]=1.Cl>C(#N)C.N1C=CC=CC=1.O.C1C=CC=CC=1>[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[S:25][CH:26]=[C:27]([NH:29][C:15]([C:14]3[NH:13][N:12]=[N:11][N:10]=3)=[O:17])[N:28]=2)[CH:19]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 147727154-Amino-2-(3-pyridyl)thiazoleHCID 178524966HCID 178524966, compound

Product 1

HCID 178522473HCID 178522473, compoundYield 38%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 6342AcetonitrileSolvent2×

Procedure

A mixture, obtained oy adding dry DMF (0.197 ml, 2.63 mmol) and then thionyl chloride (0.192 ml, 2.63 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 (333 mg, 1.75 mmol) suspended in dry acetonitrile (5 ml) under ice-cooling. The mixture was allowed to react for 15 minutes. After adding dropwise a mixed solution of 2-(3-pyridyl)4-thiazolamine (330 mg, 1.86 mmol) in dry acetonitrile (3 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. After dissolution was effected with addition of water, the reaction mixture was neutralized under ice-cooling with 2N-HCl to pH 7. The deposited solids were filtered with suction, was recrystallized from methanol-THF-water to give yellow crystals (181 mg, yield 38%) of N-(2-(3-pyridyl)-4-thiazolyl)-1H-tetrazole-5-carboxamide (Ia-23), m.p. 263°-265° C.

Workup

  1. customA mixture, obtained oy
  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. dissolutionAfter dissolution
  9. filtrationThe deposited solids were filtered with suction
  10. customwas recrystallized from methanol-THF-water

Sources & evidence

ORD record
ord-36a33e99e31e46b58cef4ccdea5e6bea
Source dataset
uspto-grants-1990_08
Patent number
US04946855

Reaction notes

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