Hydrochloric Acid → N-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidoyl chloride

HRID 69814

反応式

HRID 69814 の反応式
[OH:1][N:2]=[C:3]([C:5]1[C:9]([NH:10][CH2:11][CH2:12][O:13][CH3:14])=[N:8][O:7][N:6]=1)N.[ClH:15].[Cl-].[Na+].N([O-])=O.[Na+]>C(OCC)(=O)C.O>[OH:1][N:2]=[C:3]([Cl:15])[C:5]1[C:9]([NH:10][CH2:11][CH2:12][O:13][CH3:14])=[N:8][O:7][N:6]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 23668193Sodium NitriteHCID 136330164N'-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidamide

生成物 1

HCID 136330165N-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidoyl chloride収率 126%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
5.5 °C

実験手順

At room temperature N′-hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidamide (50.0 g, 0.226 mol) was dissolved in 6.0 M hydrochloric acid aqueous solution (250 mL, 1.5 mol). Sodium chloride (39.5 g, 0.676 mol) was added followed by water (250 mL) and ethyl acetate (250 mL). At 3-5° C. a previously prepared aqueous solution (100 mL) of sodium nitrite (15.0 g, 0.217 mol) was added slowly over 1 hr. The reaction was stirred at 3-8° C. for 2 hours and then room temperature over the weekend. LCMS indicated reaction completed. The reaction solution was extracted with ethyl acetate (2×200 mL). The combined ethyl acetate solution was dried over sodium sulfate and concentrated to give the desired product (49.9 g, 126%) as a crude white solid. LCMS for C6H10ClN4O3 (M+H)+: m/z=221.0. 1H NMR (400 MHz, DMSO-d6): δ 13.43 (s, 1 H), 5.85 (t, J=5.6 Hz, 1 H), 3.50 (t, J=5.6 Hz, 2 H), 3.37 (dd, J=10.8, 5.6 Hz, 2 H), 3.25 (s, 3 H).

後処理

  1. customroom temperature
  2. customreaction
  3. extractionThe reaction solution was extracted with ethyl acetate (2×200 mL)
  4. dry with materialThe combined ethyl acetate solution was dried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-d46416476ff14409b6d6d5c6fe94e0ee
出典データセット
uspto-grants-2014_09
特許番号
US08822511B2

関連ノート

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