Triphenylphosphine → 3-(2-bromoethyl)-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

HRID 2237489ノート

反応式

HRID 2237489 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][NH:10][S:9]1(=[O:19])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:39][CH:40](O)[CH3:41].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:39][CH2:40][CH2:41][N:10]1[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[S:9]1(=[O:19])=[O:18]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 14202443Ethanol, 1-bromo-HCID 685811711-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

生成物 1

HCID 685822933-(2-bromoethyl)-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide収率 67.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.46 g, 1.7 mmol) in tetrahydrofuran (20 mL) was cool to 0° C. and treated with triphenylphosphine (0.65 g, 2.5 mmol), bromoethanol (0.25 mL, 3.5 mmol) and diisopropyl azodicarboxylate (0.5 mL, 2.6 mmol). After the final addition, the reaction mixture was warmed to room temperature for 2 h, evaporated to a brown oil. The crude product residue was purified by flash chromatography (SiO2, 3-50% ethyl acetate/heptane) to afford 3-(2-bromoethyl)-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.44 g, 63%) as a white solid:

後処理

  1. additionAfter the final addition
  2. customevaporated to a brown oil
  3. customThe crude product residue was purified by flash chromatography (SiO2, 3-50% ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-f49ace44da1142ada44b4a31993ef303
出典データセット
uspto-grants-2010_05
特許番号
US07718652B2

反応ノート

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