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Triethylamine → 2-Methanesulfonylamino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole

HRID 974042
Notes
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Reaction equation

HRID 974042 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[CH3:8])[N:6]=1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>O1CCCC1.O>[CH3:29][S:30]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:11]([F:21])[CH:10]=2)[CH3:8])[N:6]=1)(=[O:32])=[O:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 104699822-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole

Product 1

HCID 156760492-Methanesulfonylamino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazoleYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a mixture of 2-amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (500 mg, 1.68 mmol) and triethylamine (340 mg, 3.36 mmol) in tetrahydrofuran was added methanesulfonyl chloride (385 mg, 3.36 mmol) by portion and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water, extracted with ethyl acetate and evaporated under reduced pressure to a residue, which was chromatographed and then recrystallized to afford 2-methanesulfonylamino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (447 mg, 71% yield): mp 127.5°-129.0° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customevaporated under reduced pressure to a residue, which
  3. customwas chromatographed
  4. customrecrystallized

Sources & evidence

ORD record
ord-b80f39058228437794815f77022f2f1d
Source dataset
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05066666

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes