Ammonium Chloride → Carbamic acid, N-(5-iodo-4-methyl-2-thiazolyl)-, 1,1-dimethylethyl ester

HRID 1009031Notes

Reaction equation

HRID 1009031 reaction equation
[I:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[CH3:8].[O:9](C(OC(C)(C)C)=O)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=O.C([O-])(O)=O.[Na+].[NH4+].[Cl-]>CC(O)(C)C.CN(C1C=CN=CC=1)C>[C:13]([O:12][C:10](=[O:9])[NH:7][C:5]1[S:6][C:2]([I:1])=[C:3]([CH3:8])[N:4]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 233417955-Iodo-4-methyl-2-thiazolamine

Product 1

HCID 86630949Carbamic acid, N-(5-iodo-4-methyl-2-thiazolyl)-, 1,1-dimethylethyl esterYield 58.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6386tert-ButanolSolvent

Procedure

The above prepared 5-iodo-4-methyl-thiazol-2-ylamine (2.768 g, 12 mmol) was dissolved in 30 mL of tBuOH and treated successively with BOC2O (3.02 g, 1.2 eq.), DMAP (0.141 g, 0.1 eq.), and NaHCO3 (3.39 g, 3.5 eq.). After stirring for 18 h at ambient temperature, the reaction mixture was poured onto icewater/NH4Cl, twofold extracted with ethyl acetate, washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Ensuing flash chromatography (SiO2, hexane/ethyl acetate=8/2), yielded finally 2.383 g of the title compound as off-white foam.

Workup

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

Sources & evidence

ORD record
ord-d42928a5b8c54e4cb7ba433b660b97a9
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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