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Oxalyl chloride → N-(4-Chloro-3-methyl-5-isothiazolyl)-2-(2,2-dimethylpropyl)-5-benzoxazoleacetamide

HRID 48151
Notes
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Reaction equation

HRID 48151 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][C:7]=2[N:8]=1.C(Cl)(=O)C(Cl)=O.[NH2:25][C:26]1[S:30][N:29]=[C:28]([CH3:31])[C:27]=1[Cl:32]>ClCCl.CN(C)C=O.C(OCC)(=O)C>[Cl:32][C:27]1[C:28]([CH3:31])=[N:29][S:30][C:26]=1[NH:25][C:14](=[O:16])[CH2:13][C:10]1[CH:11]=[CH:12][C:6]2[O:5][C:4]([CH2:3][C:2]([CH3:1])([CH3:18])[CH3:17])=[N:8][C:7]=2[CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 112405714-Chloro-3-methyl-1,2-thiazol-5-amineHCID 22742085[2-(2,2-Dimethylpropyl)-1,3-benzoxazol-5-yl]acetic acid

Product 1

HCID 22742093N-(4-Chloro-3-methyl-5-isothiazolyl)-2-(2,2-dimethylpropyl)-5-benzoxazoleacetamideYield 28.7%

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Catalyst
HCID 6344DichloromethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

[2-(2,2-Dimethylpropyl)benzoxazol-5-yl]acetic acid [from step 7] (0.800 g, 0.003 mole) was suspended in dichloromethane (10 ml) and N,N-dimethylformamide (one drop) and oxalyl chloride (0.451 g, 0.004 mole) were added sequentially. The mixture was stirred for 2 hour and then the solvent was removed in vacuo. The residue was taken up in xylene (10 ml), 5-amino-4-chloro-3-methylisothiazole [from step 1] (0.829 g, 0.006 mole) was added and then the mixture was heated under reflux for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with brine. The organic solution was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was further purified by flash column chromatography on silica gel, eluting with a 2:1 mixture of hexane:ethyl acetate, to give N-(4-chloro-3-methylisothiazol-5-yl)-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]acetamide (0.325 g) as a pale orange solid, m.p. 144-145° C.

Workup

  1. customthe solvent was removed in vacuo
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. washwashed with brine
  5. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo
  8. customThe residue was further purified by flash column chromatography on silica gel
  9. washeluting with a 2:1 mixture of hexane

Sources & evidence

ORD record
ord-990a42d2922f47be86b39cda0187f00b
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06703347B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes