1-Chloroethyl chloroformate → HCID 68468807, 화합물

HRID 2237437노트

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HRID 2237437 반응식
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]

참가 물질

6

반응물 2

HCID 5213051-Chloroethyl chloroformateHCID 58256121HCID 58256121, 화합물

생성물 1

HCID 68468807HCID 68468807, 화합물수율 54%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

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온도
22 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-47fed3f43d0c4826bf0d86082a9fe136
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718647B2

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