Sodium Hydroxide → Methyl 5-ethyl-1,3-thiazole-4-carboxylate

HRID 388910ノート

反応式

HRID 388910 の反応式
N([O-])=O.[Na+].N[C:6]1[S:7][C:8]([CH2:15][CH3:16])=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=1.[OH-].[Na+]>O.O[PH2]=O.C([O-])(O)=O.[Na+]>[CH2:15]([C:8]1[S:7][CH:6]=[N:10][C:9]=1[C:11]([O:13][CH3:14])=[O:12])[CH3:16]

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 737585Methyl 2-amino-5-ethyl-1,3-thiazole-4-carboxylateHCID 23668193Sodium Nitrite

生成物 1

HCID 13015585Methyl 5-ethyl-1,3-thiazole-4-carboxylate

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 516892Sodium Bicarbonate溶媒HCID 4124402Phosphinic Acid溶媒

反応条件

温度
0 °C

実験手順

The following diazotization step was adapted from Barton, A. et al., J.C.S. Perkin Trans I, 159-164 (1982): A solution of NaNO2 (150 mg, 2.17 mmol) in water (1.0 mL) was added dropwise to a stirred, cold (0° C.) solution of methyl 2-amino-5-ethyl-1,3-thiazole-4-carboxylate (186 mg, 1.0 mmol) in 50% H3PO2 (3.2 mL). The mixture was stirred at 0° C. for 1 h and allowed to warm up to room temperature where it stirred further for 2 h. After recooling to 0° C., the mixture was treated slowly with a solution of NaOH (85 mg) in water (10 mL). The mixture was then diluted with saturated NaHCO3 solution and extracted twice with ether. The organic layers were combined, dried over MgSO4 and concentrated to give methyl 5-ethylthiazole-4-carboxylate (i.e., Cap-173, Step a) (134 mg, 78%) as an orange oil (85% pure) which was used directly in the next reaction. Rt=1.58 min (Cond.-MD1); LC-MS: Anal. Calcd. for [M+H]+ C2H10NO2S: 172.05. found: 172.05.

後処理

  1. temperatureto warm up to room temperature where it
  2. stirringstirred further for 2 h
  3. customAfter recooling to 0° C.
  4. extractionextracted twice with ether
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-02814e63477445f6807dae32ea983923
出典データセット
uspto-grants-2013_02
特許番号
US08377980B2

反応ノート

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