Dimethyl-1,3-thiazole-5-carboxylic acid → HCID 19782022, compound

HRID 257855Notes

Reaction equation

HRID 257855 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.[CH2:11]([O:13][C:14]1[CH:28]=[CH:27][C:17]([O:18][C:19]2[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1)[CH3:12]>C(Cl)(Cl)Cl>[CH2:11]([O:13][C:14]1[CH:28]=[CH:27][C:17]([O:18][C:19]2[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:8]([C:4]3[S:3][C:2]([CH3:1])=[N:6][C:5]=3[CH3:7])=[O:10])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1)[CH3:12]

Participants

4

Reactant 2

HCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 196273204-(4-Ethoxyphenoxy)benzenemethanamine

Product 1

HCID 19782022HCID 19782022, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture of 2,4-dimethyl-1,3-thiazole-5-carboxylic acid (156 mg, 0.993 mM) and chloroform (20 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimde (190 mg, 0.393 mM) at 0°-10° C., and the mixture was stirred for 30 min at the same temperature. To this was added a solution (10 ml) of 4-(4-ethoxyphenoxy)benzylamine (242 mg, 0.993 mM) in chloroform at 0°-10° C., and the mixture was stirred for 12 h at the room temperature. The mixture was poured into ice water, and the mixture was extracted with chloroform. The extract was washed with saturated ammonium chloride solution and brine, dried with magnesium sulfate, and concentrated in vacuo. The residue was chromatographed over silica gel to give N-[4-(4-ethoxyphenoxy)benzyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide (171 mg, 45%) as colorless crystals, m.p. 99°-101° C.

Workup

  1. additionwas added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimde (190 mg, 0.393 mM) at 0°-10° C.
  2. stirringthe mixture was stirred for 12 h at the room temperature
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with saturated ammonium chloride solution and brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-8dcceae3076841b6b364a8dbcc6bbe61
Source dataset
uspto-grants-1993_11
Patent number
US05264448

Reaction notes

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