Hydrochloric Acid → 2-(2,4-Dinitrobenzamido)acetic acid

HRID 1399428

反応式

HRID 1399428 の反応式
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].C([O-])([O-])=O.[Na+].[Na+].[N+:12]([C:15]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18])([O-:14])=[O:13].Cl>O.O1CCOCC1>[N+:12]([C:15]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:16]=1[C:17]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:18])([O-:14])=[O:13]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 10340Sodium CarbonateHCID 884012,4-Dinitrobenzoyl chloride

生成物 1

HCID 446655292-(2,4-Dinitrobenzamido)acetic acid収率 93.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To an ice cold suspension of glycine (1.01 g, 13.56 mmol) in water (20 mL) was added Na2CO3 (1.437 g, 13.56 mmol) and stirred for 10 min. A solution of 2,4-dinitrobenzoyl chloride (prepared from 2,4-dinitrobenzoic acid, 2.3 g with SOCl2, 20 mL) in dioxane (20 mL) was added to the above solution and stirred at rt for 4 h. The reaction mixture was diluted with ice cold water and acidified with cold dil. HCl (pH: 6.0). The solution was extracted with EtOAc (5×100 mL) and the combined organic layer was dried over anhyd Na2SO4 and filtered. The solution was evaporated and the residue was chromatographed over silica gel column using chloroform:methanol (95:5) as eluents to give the product as a white color solid (2.5 g, 85%), mp 188-190° C. 1H NMR (400 MHz, DMSO-d6): δ 12.79 (1H, br s), 9.29 (1H, t, J=5.4 Hz), 8.77 (1H, d, J=2.0 Hz), 8.64 (1H, dd, J=8.4, 2.0 Hz), 7.89 (1H, d, J=8.4 Hz), 3.99 (2H, d, J=6.0 Hz); LC-MS (negative ion mode): m/z 268 (M−H)−.

後処理

  1. stirringstirred at rt for 4 h
  2. additionThe reaction mixture was diluted with ice cold water
  3. extractionThe solution was extracted with EtOAc (5×100 mL)
  4. dry with materialthe combined organic layer was dried over anhyd Na2SO4
  5. filtrationfiltered
  6. customThe solution was evaporated
  7. customthe residue was chromatographed over silica gel column

出典と根拠

ORDレコード
ord-392e87f112624ab5a96d4a1ca166b820
出典データセット
uspto-grants-2014_12
特許番号
US08906344B2

関連ノート

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