Dimethylformamide → HCID 67430246, compound

HRID 410391Notes

Reaction equation

HRID 410391 reaction equation
[H-].[Na+].[Br:3][C:4]1[S:8][C:7]([C:9]2([OH:13])[CH2:12][CH2:11][CH2:10]2)=NC=1.[CH3:14]I.[CH3:16][N:17](C=O)C>C1COCC1.[NH4+].[Cl-]>[Br:3][C:4]1[S:8][C:7]([C:9]2([O:13][CH3:14])[CH2:10][CH2:11][CH2:12]2)=[CH:16][N:17]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58456224HCID 58456224, compound

Product 1

HCID 67430246HCID 67430246, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil) (47.0 mg, 1.175 mmol) was added to a 0° C. solution of Intermediate 1 (250 mg, 1.068 mmol) in DMF (3 mL) and THF (3 mL) and the mixture was allowed to react for 1 hour. Methyl iodide (0.080 ml, 1.281 mmol) was added and the mixture further reacted for 2 hours. The reaction mixture was poured in dilute aqueous NH4Cl and extracted twice with diethyl ether. The organic fraction was concentrated and the residue was passed through a plug of silica eluting with 1:10 ethyl acetate:hexane to yield 2-bromo-5-(1-methoxycyclobutyl)-1,3-thiazole (225 mg, 85%). 1H NMR (500 MHz, (CD3)2CO): δ 7.73 (s, 1H); 3.19 (s, 3H); 2.54-2.40 (m, 4H); 1.92-1.82 (m, 2H).

Workup

  1. customto react for 1 hour
  2. customthe mixture further reacted for 2 hours
  3. extractionextracted twice with diethyl ether
  4. concentrationThe organic fraction was concentrated

Sources & evidence

ORD record
ord-fb549fdb52fc4ea5912cb36c5e0c2215
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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