Hexane → tert-butyl N-(4-ethyl-5-methylsulfanyl-thiazol-2-yl)carbamate

HRID 1009054Notes

Reaction equation

HRID 1009054 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][CH3:14])[N:12]=1)([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.CCCCCC.[CH3:27][S:28]SC>C1COCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:9][C:10]([S:28][CH3:27])=[C:11]([CH2:13][CH3:14])[N:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8058HexaneHCID 12232Dimethyl DisulfideHCID 58554442(4-Ethyl-thiazol-2-yl)-carbamic acid tert-butyl esterHCID 178418339Butyllithium

Product 1

HCID 86630961tert-butyl N-(4-ethyl-5-methylsulfanyl-thiazol-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above prepared (4-ethyl-thiazol-2-yl)-carbamic acid tert-butyl ester (1.12 g, 4.90 mmol) was dissolved in 12 mL of abs. THF and treated at −78° C. with a solution of nBuLi in hexane (6.53 mL, 1.5M, 2 eq.). The reaction mixture was kept for 15 Min. at −78° C. and then allowed to reach RT. After recooling to −78° C., methyldisulfanylmethane (0.870 mL, 2 eq.) was added and the mixture kept for 30 Min. at this temperature and then slowly warmed to RT. Pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/ethyl acetate=85/15), afforded 1.067 g of the title product as off-white solid.

Workup

  1. dissolutionwas dissolved in 12 mL of abs
  2. customat −78° C.
  3. customto reach RT
  4. customAfter recooling to −78° C.
  5. additionPouring
  6. extractionice/NH4Cl, twofold extraction with ethyl acetate washing with water
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-f32678613b7b4456a4e41d110b00e0c4
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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