Dimethyl Sulfoxide → HCID 19966225、化合物

HRID 977860ノート

反応式

HRID 977860 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:17][C:16]=1[NH:25][C:26](=[O:42])[CH2:27][CH:28]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:35][C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(OCC)C.C(Cl)Cl>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]=[O:24])=[CH:17][C:16]=1[NH:25][C:26](=[O:42])[CH2:27][CH:28]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:35][C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)([CH3:14])([CH3:12])[CH3:13]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19966239N-[2-t-Butyl-5-(3-hydroxypropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

生成物 1

HCID 19966225HCID 19966225、化合物収率 88%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-78 °C

実験手順

2 ml of a methylene chloride solution containing 155 mg (1.98 mmol) of dimethyl sulfoxide were added dropwise over a period of 5 minutes to 2 ml of a methylene chloride solution containing 126 mg (0.99 mmol) of oxalyl chloride which had previously been cooled at -78° C. The mixture was then stirred for 5 minutes at this temperature, after which 15 ml of a methylene chloride solution containing 354 mg (0.825 mmol) of N-[2-t-butyl-5-(3-hydroxypropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 18) were added, and the mixture was stirred for a further 15 minutes at this temperature. 501 mg (4.95 mmol) of triethylamine were then added to the reaction mixture, which was then stirred for 5 minutes at the same temperature. The reaction mixture was then allowed to return to room temperature, after which it was diluted with diethyl ether, and washed with dilute aqueous hydrochloric acid and then with water. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 20 g of silica gel. Elution with a 100:5 by volume mixture of methylene chloride and ethyl acetate afforded 310 mg (yield 88%) of the title compound as crystals, melting at 176°-177° C. (after recrystallization from a mixture of methylene chloride and diethyl ether).

後処理

  1. additionwere added
  2. stirringthe mixture was stirred for a further 15 minutes at this temperature
  3. stirringwas then stirred for 5 minutes at the same temperature
  4. customto return to room temperature
  5. washwashed with dilute aqueous hydrochloric acid
  6. customThe solvent was then removed by distillation under reduced pressure
  7. washElution with a 100:5
  8. additionby volume mixture of methylene chloride and ethyl acetate

出典と根拠

ORDレコード
ord-b777467e2d9746c79dcc30480e31bfee
出典データセット
uspto-grants-1997_03
特許番号
US05614550

反応ノート

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