Trifluoroacetic acid → HCID 178470518、化合物

HRID 52606

反応式

HRID 52606 の反応式
FC(F)(F)C(O)=O.[N-:8]=[N+:9]=[N-:10].[Na+].[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:13]>N1C(C)=CC=CC=1C>[CH2:17]([O:16][C:14]([C:12]1[NH:13][N:10]=[N:9][N:8]=1)=[O:15])[CH3:18]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 69336Ethyl cyanoformate

生成物 1

HCID 178470518HCID 178470518、化合物収率 52.6%

試薬・触媒・溶媒 1

HCID 79372,6-Lutidine溶媒

実験手順

Trifluoroacetic acid (24.47 g, 0.21M) was added dropwise over 0.5 hr under nitrogen to a stirred suspension of sodium azide (12.59 g, 0.19M) in 2,6lutidine (100 ml) at 8° to 12°. After stirring for 7 minutes ethyl cyanoformate (20.4 g, 0.20M) was added in one portion. The mixture was heated and stirred at 75° for 6 hours and then, after cooling, stirred at 20° for 16 hr. After cooling to 10° the mixture was added to ice (250 g) and 11 molar hydrochloric add (100 ml) keeping the temperature below 20°. The product was extracted into ethyl acetate (1×250, 1×200, 2×100 ml) and the combined extracts dried over magnesium sulphate. After evaporation of the solvent under reduced pressure the oily product (38.22 g) was taken up in ether (50 ml) and hexane (25 ml) added. Storage at 4° for 2-3 days produced crystalline ethyl-1H-tetrazole-5-carboxylate that was filtered off, washed with chilled ether, and air dried, 14.12 g (52.6% yield), m.p. 88°-93°.

後処理

  1. additionwas added in one portion
  2. temperatureThe mixture was heated
  3. temperatureafter cooling
  4. stirringstirred at 20° for 16 hr
  5. temperatureAfter cooling to 10° the mixture
  6. additionhydrochloric add (100 ml)
  7. customthe temperature below 20°
  8. extractionThe product was extracted into ethyl acetate (1×250, 1×200, 2×100 ml)
  9. dry with materialthe combined extracts dried over magnesium sulphate
  10. customAfter evaporation of the solvent under reduced pressure the oily product (38.22 g)
  11. additionhexane (25 ml) added

出典と根拠

ORDレコード
ord-cd980bb000e14269a008b39af27df53a
出典データセット
uspto-grants-1997_04
特許番号
US05616721

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