Ethanol → 5-[N-(3',5'-Bistrifluoromethylbenzyl)amino]-2-methyltetrazole

HRID 390739

反応式

HRID 390739 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[CH3:17][N:18]1[N:22]=[N:21][C:20]([NH2:23])=[N:19]1.C(O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6][NH:23][C:20]1[N:21]=[N:22][N:18]([CH3:17])[N:19]=1

参加物

6

反応物 4

HCID 702EthanolHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 1386772-methyl-2H-1,2,3,4-tetrazol-5-amineHCID 4311764Sodium borohydride

生成物 1

HCID 230732215-[N-(3',5'-Bistrifluoromethylbenzyl)amino]-2-methyltetrazole収率 87.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 3,5-bis(trifluoromethyl)benzaldehyde (4 g, 16.5 mmol), 2-methyl-2H-tetrazol-5-amine (1.96 g, 19.8 mmol) and molecular sieves (5-10 Å beads) in toluene (50 mL) was heated at reflux for 4 hours, after which time the solvent was removed. Ethanol (50 mL) and sodium borohydride (1.25 g, 33 mmol) were added. The resulting mixture was stirred at room temperature for 30 minutes and then partitioned between saturated NH4Cl (50 mL) and ethyl acetate (2×50 mL). The combined organic layers were washed with saturated NaCl (50 mL), dried (MgSO4), filtered and concentrated to yield the title compound as a white solid (4.7 g). 1H NMR (400 MHz, CDCl3) δ 4.2 (s, 3 H) 4.7 (s, 1 H) 4.7 (s, 1 H) 5.0 (t, J=6.0 Hz, 1 H) 7.8 (s, 1 H) 7.9 (s, 2 H). MS (ES+) Calc: 325.08, Found: 325.8 (M+1).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customafter which time the solvent was removed
  4. custompartitioned between saturated NH4Cl (50 mL) and ethyl acetate (2×50 mL)
  5. washThe combined organic layers were washed with saturated NaCl (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-63ad3bc616ff479fa3780317a102f092
出典データセット
uspto-grants-2013_02
特許番号
US08383660B2

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