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Triethylamine → 2-Ethyl-4-methoxybenzothiazole-7-carboxylic acid (3,5-dimethylisoxazol-4-yl)amide

HRID 427295
Notes
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Reaction equation

HRID 427295 reaction equation
[CH2:1]([C:3]1[S:4][C:5]2[C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=[C:8]([O:15][CH3:16])[C:6]=2[N:7]=1)[CH3:2].C(Cl)(=O)C(Cl)=O.[CH3:23][C:24]1[C:28]([NH2:29])=[C:27]([CH3:30])[O:26][N:25]=1.C(N(CC)CC)C>ClCCl>[CH3:23][C:24]1[C:28]([NH:29][C:12]([C:11]2[C:5]3[S:4][C:3]([CH2:1][CH3:2])=[N:7][C:6]=3[C:8]([O:15][CH3:16])=[CH:9][CH:10]=2)=[O:14])=[C:27]([CH3:30])[O:26][N:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1820404-Amino-3,5-dimethylisoxazoleHCID 183570002-Ethyl-4-methoxybenzothiazole-7-carboxylic acid

Product 1

HCID 98587562-Ethyl-4-methoxybenzothiazole-7-carboxylic acid (3,5-dimethylisoxazol-4-yl)amideYield 11.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-ethyl-4-methoxybenzothiazole-7-carboxylic acid (0.1 g) in dichloromethane (10 ml) was added oxalyl chloride (0.08 ml) and dimethylformanide (1 drop). The reaction was stirred at room temperature for 16 hrs, and then the solvent was removed in vacuo to yield a brown solid residue. This was taken up in dichloromethane is (30 ml) and 3,5-dimethylisoxazol-4-amine (0.05 g) was added followed by triethylamine (0.15 ml) and the reaction stirred at room temperature for 16 hrs. The solvent was removed in vacuo and the product purified by flash chromatography (eluent ethyl acetate) to yield the title compound as an off-white solid (0.016 g). TLC Rf 0.38 (ethyl acetate); Mpt 85-87° C.

Workup

  1. customthe solvent was removed in vacuo
  2. customto yield a brown solid residue
  3. additionwas added
  4. stirringthe reaction stirred at room temperature for 16 hrs
  5. customThe solvent was removed in vacuo
  6. customthe product purified by flash chromatography (eluent ethyl acetate)

Sources & evidence

ORD record
ord-87f7f21d60a34c1ea673d11d379c6062
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06313116B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes