11-Bromoundecanoic acid → N3(CH2)10C(O)Cl

HRID 1160642

反応式

HRID 1160642 の反応式
BrCCCCCCCCCCC(O)=O.[N-]=[N+]=[N-].[Na+].[N:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=O)=[N+:20]=[N-:21].C(Cl)(=O)C([Cl:38])=O>CN(C=O)C.[Cl-].[Na+].O.C1C=CC=CC=1.CCOCC>[N:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([Cl:38])=[O:34])=[N+:20]=[N-:21]

参加物

9

反応物 4

HCID 1781211-Bromoundecanoic acidHCID 33557Sodium AzideHCID 65578Oxalyl chlorideHCID 45409411-Azidoundecanoic acid

生成物 1

HCID 22283452N3(CH2)10C(O)Cl

試薬・触媒・溶媒 4

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

In a glass reaction vessel, 10.6 grams (40 mmol) of 11-Bromoundecanoic acid was dissolved in 225 milliliters DMF and 26 grams (400 mmol) sodium azide was added. The resulting stirred mixture was heated to 80° C. for 16h, and then the reaction mixture was worked up with ether and brine. The ether layer was dried (MgSO4), filtered, and concentrated to 9.5 grams of N3(CH2)10C(O)OH as a pale yellow oil which was used without purification. In a glass reaction vessel, the N3(CH2)10C(O)OH was dissolved in 120 milliliters benzene and 12.7 grams (100 mmol) oxalyl chloride was added. The reaction was allowed to stir for 20 h, at which time the volatiles were removed in vacuo. The resulting residue was dissolved in pentane and filtered in a nitrogen atmosphere to remove solids. Concentration of the filtrate afforded N3(CH2)10C(O)Cl as a clear, yellow oil.

後処理

  1. dry with materialThe ether layer was dried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated to 9.5 grams of N3(CH2)10C(O)OH as a pale yellow oil which
  4. customwas used without purification
  5. customIn a glass reaction vessel
  6. stirringto stir for 20 h, at which time the volatiles
  7. customwere removed in vacuo
  8. dissolutionThe resulting residue was dissolved in pentane
  9. filtrationfiltered in a nitrogen atmosphere
  10. customto remove solids

出典と根拠

ORDレコード
ord-d2c58d9a204b43458f0f60bc29f43dfd
出典データセット
uspto-grants-2010_10
特許番号
US07816473B2

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