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Diisopropylamine → N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea

HRID 974054
Notes
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Reaction equation

HRID 974054 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[NH2:21][C:22]1[S:23][CH:24]=[C:25]([CH:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:31]([F:41])[CH:30]=2)[CH3:28])[N:26]=1.[CH3:42][N:43]=[C:44]=[S:45]>O1CCCC1>[CH3:42][NH:43][C:44]([NH:21][C:22]1[S:23][CH:24]=[C:25]([CH:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[C:31]([F:41])[CH:30]=2)[CH3:28])[N:26]=1)=[S:45]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 11167Methyl isothiocyanateHCID 2724682Lithium diisopropylamideHCID 104699822-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazoleHCID 178418339Butyllithium

Product 1

HCID 15676068N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea
Yield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To lithium diisopropylamide in tetrahydrofuran prepared with diisopropylamine (0.187 g, 1.85 mmol) and n-butyllithium (1.9 mmol) was added 2-amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (0.50 g, 1.68 mmol) in tetrahydrofuran at -70° C. After the mixture was stirred for 20 min, methylisothiocyanate (0.131 g, 1.8 mmol) in tetrahydrofuran was added to the mixture. After the mixture was stirred at room temperature for 3.5 h, the mixture was evaporated under reduced pressure to a residue, which was extracted with chloroform. The extracts were washed with water, dried over, and evaporated under reduced pressure to a residue, which was chromatographed and recrystallized to afford N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea (0.233 g, 35% yield) as crystalline material: mp 180.5°-181.0° C.

Workup

  1. stirringAfter the mixture was stirred at room temperature for 3.5 h
  2. customthe mixture was evaporated under reduced pressure to a residue, which
  3. extractionwas extracted with chloroform
  4. washThe extracts were washed with water
  5. customdried over, and
  6. customevaporated under reduced pressure to a residue, which
  7. customwas chromatographed
  8. customrecrystallized

Sources & evidence

ORD record
ord-5a9e03d33fb94f99a0834fbff72218cf
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