Hydrochloric Acid → HCID 178423991, compound

HRID 1708941Notes

Reaction equation

HRID 1708941 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[CH:24]=[CH:23][C:22]([C:25]2[S:26][CH:27]=[C:28]([NH2:30])[N:29]=2)=[CH:21][CH:20]=1.Cl>C(#N)C.N1C=CC=CC=1.O.C1C=CC=CC=1>[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[S:26][CH:27]=[C:28]([NH:30][C:15]([C:14]3[NH:13][N:12]=[N:11][N:10]=3)=[O:17])[N:29]=2)=[CH:23][CH:24]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 147727022-(4-Methylphenyl)-4-thiazolamineHCID 178524966HCID 178524966, compound

Product 1

HCID 178423991HCID 178423991, compoundYield 52%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 6342AcetonitrileSolvent2×

Procedure

A mixture, obtained by adding ice-cooled dry DMF(0.53 ml, 6.48 mmol) and then thionyl chloride (0.499 ml, 6.84 mmol) to dry benzene (1.5 ml,, 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 (867 mg, 4.56 mmol) suspended in dry acetonitrile (15 ml) under ice-cooling. The mixture was allowed to react for 15 minutes. After adding dropwise a mixed solution of 2-(4-methylphenyl)-4-thiazolamine (928 mg, 4.88 mmol) in dry acetonitrile (15 ml) and dry pyridine (4 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 acidified under ice-cooling with 2N-HCl to pH 2. The deposited solids were filtered with suction, washed with water and recrystallized from methanol-water to give yellowish crystals (677 mg. yield 52%) of N-(2-(4-methylphenyl)-4-thiazolyl)-1H-tetrazole-5-carboxamide (Ia-5), m.p.228°-230° C.

Workup

  1. customA mixture, obtained
  2. additionby adding ice-
  3. customto react for 10 minutes upon which the mixture
  4. customseparated into two layers
  5. temperaturecooling
  6. customto react for 15 minutes
  7. temperatureto warm up to room temperature
  8. customto react for 1 hour
  9. dissolutionAfter dissolution
  10. filtrationThe deposited solids were filtered with suction
  11. washwashed with water
  12. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-b19f4e1c0a1441768b389cf072ca1ec9
Source dataset
uspto-grants-1990_08
Patent number
US04946855

Reaction notes

Loading…