Methanesulfonyl chloride → Ethyl 2-[(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate

HRID 14335Notes

Reaction equation

HRID 14335 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.C(N(CC)C(C)C)(C)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([NH:1][C:2]1[O:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 319549Ethyl 2-amino-1,3-oxazole-4-carboxylate

Product 1

HCID 21086093Ethyl 2-[(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 ml screw cap vial was added (1 g, 5.8069 mmoles) ethyl 2-amino-1,3-oxazole-4-carboxylate, (10 ml) dichloromethane and (1.39 ml, 7.9797 mmoles, 1.25 eq.) N,N-diisopropylethylamine. To the reaction was then added (0.545 ml, 7.0415 mmoles, 1.1 eq.) methanesulfonyl chloride, and the reaction was agitated for 14 hours. The reaction was then evaporated to dryness and purified using a Biotage silica gel column, resulting in (272 mg) of ethyl 2-[(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate.

Workup

  1. customTo a 20 ml screw cap
  2. customThe reaction was then evaporated to dryness
  3. custompurified
  4. customresulting in (272 mg) of ethyl 2-[(methylsulfonyl)amino]-1,3-oxazole-4-carboxylate

Sources & evidence

ORD record
ord-d9638ebdcd4f4839b8b9e1f57a937acf
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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