1-Chloroethyl chloroformate → HCID 68468807、化合物

HRID 2237437ノート

反応式

HRID 2237437 の反応式
C([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([Cl:19])=[C:16]([Cl:18])[S:17][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C.C(Cl)Cl.CO>[ClH:18].[Cl:18][C:16]1[S:17][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[Cl:19]

参加物

6

反応物 2

HCID 5213051-Chloroethyl chloroformateHCID 58256121HCID 58256121、化合物

生成物 1

HCID 68468807HCID 68468807、化合物収率 54%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
22 °C

実験手順

A solution of the product from step g) (727 mg, 2.33 mmol) in anhydrous dichloroethane (11.6 ml) was cooled to 0° C., treated with 1-Chloroethyl chloroformate (1.27 ml, 11.65 mmol) and the reaction was warmed to 22° C. for 1 hour. The reaction diluted with CH2Cl2 (50 ml) and washed with sat. NaHCO3 (25 ml). The sat. NaHCO3 was back extracted with CH2Cl2 and the combined organic layers were washed with brine (25 ml), dried (MgSO4) and concentrated providing an oily residue, which was taken up in anhydrous MeOH (75 ml) and refluxed for 1 hour. The MeOH was evaporated and the crude residue was triturated with ether and filtered providing 323 mg (54%) of the subtitle compound. 1H NMR (300 MHz, DMSO) δ 9.60 (br s, 2H); 3.14-3.28 (m, 6H); 2.97-3.50 (m, 2H); MS: ESI (positive): 222, 224 (M+H).

後処理

  1. washwashed with sat. NaHCO3 (25 ml)
  2. extractionThe sat. NaHCO3 was back extracted with CH2Cl2
  3. washthe combined organic layers were washed with brine (25 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customproviding an oily residue, which
  7. temperaturerefluxed for 1 hour
  8. customThe MeOH was evaporated
  9. customthe crude residue was triturated with ether
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-47fed3f43d0c4826bf0d86082a9fe136
出典データセット
uspto-grants-2010_05
特許番号
US07718647B2

反応ノート

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