2-Aminothiazole → Methyl 4-[(thiazol-2-ylamino)acetyloxy]benzoate

HRID 1599939Notes

Reaction equation

HRID 1599939 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)(O)=O.C(Cl)(=O)C(Cl)=[O:18].[NH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1.CCN(C(C)C)C(C)C>C1C=CC=CC=1.CN(C=O)C.CCOC(C)=O>[S:24]1[CH:25]=[CH:26][N:27]=[C:23]1[NH:22][CH2:1][C:4]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=1)=[O:18]

Participants

8

Reactant 4

HCID 21552-AminothiazoleHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 138161514-(Carboxymethoxy)-benzoic acid 1-methyl ester

Product 1

HCID 18928580Methyl 4-[(thiazol-2-ylamino)acetyloxy]benzoate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acid 24-2 (1.0 g, 5 mmol) was suspended in 25 mL benzene, a few drops of DMF were added, then oxalyl chloride (1.3 ml, 15 mmol) in two portions. Once the gas evolution stopped, the homogeneous solution was concentrated, diluted with 25 mL DMF, and treated with 2-aminothiazole (550 mg, 5.5 mmol) and DIPEA (1 mL, 5.7 mmol). This mixture was stirred for 16 h, diluted with EtOAc, washed with water, sat. NaHCO3, and brine, dried (MgSO4) and concentrated providing 24-3 as an orange solid.

Workup

  1. concentrationthe homogeneous solution was concentrated
  2. additiondiluted with 25 mL DMF
  3. washwashed with water, sat. NaHCO3, and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-09d7ffff355c4e93a2431041b8fe0720
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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