Sodium Hydroxide → Ethyl acetate methanol ammonia

HRID 890909ノート

反応式

HRID 890909 の反応式
[N:1]([O-])=O.[Na+].N(O)=[O:6].Cl.Cl.[C:10]1(N[CH2:21][CH2:22]N)C2C(=CC=CC=2)C=CC=1.N[C:25]1[C:33]2N=NNC=2C=CC=1.[OH-:34].[Na+]>Cl.C([O-])(=O)C.[Na+].CC(C)=O>[CH3:33][CH2:25][O:34][C:21]([CH3:22])=[O:6].[CH3:10][OH:34].[NH3:1]

参加物

9

反応物 5

HCID 14798Sodium HydroxideHCID 15106N-1-Naphthylethylenediamine dihydrochlorideHCID 24529Nitrous AcidHCID 23668193Sodium Nitrite2 回HCID 178507462HCID 178507462、化合物

生成物 1

HCID 21873639Ethyl acetate methanol ammonia収率 66%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 313Hydrochloric Acid溶媒HCID 517045Sodium Acetate溶媒

実験手順

In more detail, to provide N1-[4-(5-Azobenzotriazoyl)phenyl]-ethane-1,2-diamine (=Compound 1), 5-Aminobenzotriazole (0.854 g, 1.1 eq, 6.37 mmol) was dissolved in HCl (5ml, 50% v/v) and diazotised by dropwise addition of sodium nitrite (0.484 g, 1.2 eq, in 5 ml H2O) at 0° C. An excess of sodium nitrite was detected using starch iodide paper. A dark blue colour indicated excess nitrous acid which inferred the formation of the diazonium salt. Separately N-(1-Naphthyl) ethylenediamine dihydrochloride (1.500 g, 5.79 mmol) was dissolved in sodium acetate buffer (1.0M, 60 ml, pH 6.0) and acetone (80 ml). Diazotised aminobenzotriazole (1.1 eq) was added to this solution dropwise at 0° C. with stirring over 1 hour after which the solution was neutralised by addition of sodium hydroxide (2M). The solid produced was isolated by filtration and washed with sat. KCl (3×50 ml) prior to purification by trituration using methanol and diethyl ether to produce the title compound as an orange solid in 66% yield Rf (EtOAc/CH3OH/NH3 5/1/1) 0.14; dH (270 MHz, CD3OH) 3.00 (2H, t, CH2) 3.48 (2H, t, CH2) 6.69 (1H, dd, arH) 7.51 (1H, t, arH) 7.63 (1H, t, arH) 7.87 (1H, d, arH) 7.94 (2H, m, arHs) 8.13 (1H, d, arH) 8.34 (1H, s, arH) 9.02 (1H, d, arH); dc(270 MHz, CD3OD) 41.40 (CH2) 47.01 (CH2) 104.26 (CH) 114.93 (CH) 115.13 (CH) 116.67 (CH) 117.47 (CH) 122.20 (CH) 124.26 (C) 124.73 (CH) 126.03 (CH) 127.91 (CH) 134.62 (C) 139.91 (C) 146.12 (C) 146.76 (C) 148.98 (C) 151 28 (C); FAB ms m/z 332.1621 [C18H18N7 (M+1) <0.1 ppm].

後処理

  1. customThe solid produced
  2. customwas isolated by filtration
  3. washwashed with sat. KCl (3×50 ml)
  4. customto purification by trituration

出典と根拠

ORDレコード
ord-06ec18926999491cb25f99b65b58f0b3
出典データセット
uspto-grants-2006_02
特許番号
US07001721B1

反応ノート

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