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

Participants

Role	Name	HCID	Charge
Reactant	Ammonium Chloride	HCID 25517	—
Reactant	Di-tert-butyl dicarbonate	HCID 90495	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	4-Ethyl-1,3-thiazol-2-amine	HCID 12378205	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	tert-Butanol	HCID 6386	—
Product	(4-Ethyl-thiazol-2-yl)-carbamic acid tert-butyl ester	HCID 58554442	76.4%

Reaction Conditions

Temperature	40 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07973051B2
Source dataset	uspto-grants-2011_07
ORD ID	ord-e38f6d8c5f7343aa9730c5574f8458b0
Source note	uspto-grants-2011_07