Acetyl chloride → 3-(4-Benzyloxy-2-iodo-5-methoxyphenyl)-5-methyl-[1,2,4]oxa-diazole

HRID 2075947ノート

反応式

HRID 2075947 の反応式
[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:12]([C:13]([NH:15][OH:16])=[NH:14])=[C:11]([I:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](N(CC)CC)[CH3:23].C(Cl)(=O)C>O1CCCC1>[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:12]([C:13]2[N:14]=[C:22]([CH3:23])[O:16][N:15]=2)=[C:11]([I:21])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178492429HCID 178492429、化合物

生成物 1

HCID 508988613-(4-Benzyloxy-2-iodo-5-methoxyphenyl)-5-methyl-[1,2,4]oxa-diazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 4-benzyloxy-N-hydroxy-2-iodo-5-methoxy-benzamidine (reference example 3-1) (35 g), triethylamine (31 mL) and tetrahydrofuran (31 mL) was added acetyl chloride (8.2 mL) under ice-bath cooling. The mixture was stirred at the same temperature for 1 hour. Insoluble materials were removed by filtration. To the filtrate was added tetrabutylammonium fluoride (1 mol/L tetrahydrofuran solution, 89 mL). After stirring at the same temperature for 2 hours, water and ethylacetate were added to the mixture. The separated organic layer was washed with 1 mol/L hydrochloric acid, a 1 mol/L aqueous solution of sodium hydroxide, an aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with methanol to give the title compound (31.5 g).

後処理

  1. temperaturecooling
  2. customInsoluble materials were removed by filtration
  3. additionTo the filtrate was added tetrabutylammonium fluoride (1 mol/L tetrahydrofuran solution, 89 mL)
  4. stirringAfter stirring at the same temperature for 2 hours
  5. additionwater and ethylacetate were added to the mixture
  6. washThe separated organic layer was washed with 1 mol/L hydrochloric acid
  7. dry with materiala 1 mol/L aqueous solution of sodium hydroxide, an aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with methanol

出典と根拠

ORDレコード
ord-887054f1f7e24df78e04b7dae8830449
出典データセット
uspto-grants-2011_04
特許番号
US07923462B2

反応ノート

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