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

HRID 1009031노트

반응식

HRID 1009031 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6386tert-Butanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d42928a5b8c54e4cb7ba433b660b97a9
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973051B2

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