Ammonium Chloride → (4-Ethyl-thiazol-2-yl)-carbamic acid tert-butyl ester

HRID 1009053Notes

Reaction equation

HRID 1009053 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([NH2:8])[S:6][CH:7]=1)[CH3:2].C([O-])(O)=O.[Na+].[O:14](C(OC(C)(C)C)=O)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O.[NH4+].[Cl-]>CC(O)(C)C.CN(C1C=CN=CC=1)C>[C:18]([O:17][C:15](=[O:14])[NH:8][C:5]1[S:6][CH:7]=[C:3]([CH2:1][CH3:2])[N:4]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 123782054-Ethyl-1,3-thiazol-2-amine

Product 1

HCID 58554442(4-Ethyl-thiazol-2-yl)-carbamic acid tert-butyl esterYield 76.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

The above prepared 4-ethyl-thiazol-2-ylamine (1.50 g, 11.7 mmol) was dissolved in 23 mL of tBuOH and treated successively with DMAP (0.143 g, 0.1 eq.), NaHCO3 (2.46 g, 2.5 eq.) and BOC2O (2.81 g, 1.1 eq.). After stirring for 0.5 h at 40° C., the reaction mixture was poured onto icewater/NH4Cl, twofold extracted with ethyl acetate, washed with water, dried over sodium sulfate, and evaporated to dryness. Ensuing flash chromatography (SiO2, heptane/ethyl acetate=85/15), yielded finally 2.04 g of the title compound as yellow solid.

Workup

  1. extractiontwofold extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-e38f6d8c5f7343aa9730c5574f8458b0
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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