Trichloroisocyanuric Acid → HCID 57912300、化合物

HRID 1499328ノート

反応式

HRID 1499328 の反応式
[C:1]([O-:4])(O)=[O:2].[Na+].[N+:6]([C:9]1[C:14]([CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:13][CH:12]=[CH:11][C:10]=1CO)([O-:8])=[O:7].[Na+].[Br-].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>CC(C)=O.CC1(C)N([O])C(C)(C)CCC1.CC(O)C>[Si:17]([O:16][CH2:15][C:14]1[C:9]([N+:6]([O-:8])=[O:7])=[C:10]([CH:11]=[CH:12][CH:13]=1)[C:1]([OH:4])=[O:2])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

参加物

8

反応物 4

HCID 6909Trichloroisocyanuric AcidHCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 57912293HCID 57912293、化合物

生成物 1

HCID 57912300HCID 57912300、化合物収率 56%

試薬・触媒・溶媒 3

HCID 2724126Tempo触媒HCID 180Acetone溶媒HCID 3776Isopropanol溶媒

実験手順

An aqueous solution of 15% NaHCO3 (18 mL) was added to a stirring solution of Compound 9 (1.80 g, 2.69 mmol) in acetone (60 mL) at 0° C. NaBr (133 mg, 1.29 mmol) and TEMPO (18.9 mg, 0.121 mmol) were then added followed by the slow addition of trichloroisocyanuric acid (2.81 g, 12.1 mmol). The resulting solution was allowed to warm to room temperature and stirring for 1 d after which time 2-propanol (3.63 mL) was added. The mixture was filtered over Celite, concentrated on a rotary evaporator, dissolved in 18 mL of saturated Na2CO3, washed with EtOAc (3×10 mL), acidified with 1 M HCl, and extracted with ethyl acetate (3×50 mL). The resulting organics were dried over Na2SO4, filtered, concentrated on a rotary evaporator and purified by silica gel chromatography (10% MeOH:CH2Cl2) to yield Compound 10 (1.05 g, 56%) as a white solid.

後処理

  1. additionwas added
  2. filtrationThe mixture was filtered over Celite
  3. concentrationconcentrated on a rotary evaporator
  4. dissolutiondissolved in 18 mL of saturated Na2CO3
  5. washwashed with EtOAc (3×10 mL)
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. dry with materialThe resulting organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated on a rotary evaporator
  10. custompurified by silica gel chromatography (10% MeOH:CH2Cl2)

出典と根拠

ORDレコード
ord-411387c1951a4c73bad69464089e4eb3
出典データセット
uspto-grants-2015_12
特許番号
US09200097B2

反応ノート

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