Triethylamine → HCID 376100, 화합물

HRID 1899059노트

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HRID 1899059 반응식
O[CH2:2][CH2:3][N:4]([C:8]1[C:9]([N+:21]([O-:23])=[O:22])=[CH:10][C:11]([N+:18]([O-:20])=[O:19])=[C:12]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:13]=1)[CH2:5][CH2:6]O.CCN(CC)CC.CS([Cl:35])(=O)=O.[Li+].[Cl-:37]>C1COCC1.CCOC(C)=O.CN(C=O)C>[Cl:37][CH2:2][CH2:3][N:4]([C:8]1[C:9]([N+:21]([O-:23])=[O:22])=[CH:10][C:11]([N+:18]([O-:20])=[O:19])=[C:12]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:13]=1)[CH2:5][CH2:6][Cl:35]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 10360491HCID 10360491, 화합물

생성물 1

HCID 376100HCID 376100, 화합물수율 69.9%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
130 °C

실험 절차

A stirred solution of the above diol (IX) (1.90 g, 5.43 mmol) and Et3N (1.90 mL, 14 mmol) in dry THF (60 mL) was treated dropwise at 0° C. with methanesulfonyl chloride (0.89 mL, 11 mmol). After a further 15 min, the solution was diluted with EtOAc, washed well with water, and worked up to give the crude dimesylate (Id: X=OSO2Me, R=SO2NH2). This was immediately dissolved in DMF (50 mL) containing LiCl (20 g), and the mixture stirred at 130° C. for 15 min before solvent was removed under reduced pressure. The residue was partitioned between EtOAc and water, and the organic layer was worked up and chromatographed on silica gel. Elution with EtOAc gave 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzenesulfonamide (18) (Id: X=Cl, R=SO2NH2) (1.47 g, 64%), mp 153°-154° C. (EtOAc/petroleum ether). 1H NMR ((CD3)2CO) δ 8.54. (S, 1H, H-3), 7.99 (br, 2H, SO2NH2), 7.91 (S, 1H, H-6), 3.84 (t, J=5.6 Hz, 4H, CH2Cl), 3.67 (t, J=5.6 Hz, 4H, CH2N). 13C NMR ((CD3)2CO) δ 146.13 (C-5), 140.64 (C-1), 138.86, 136.93 (C-2,4), 124.95, 121.77 (C-3,6), 52.47 (CH2N), 41.62 (CH2Cl). Anal. (C10H12Cl2N4O6S) C,H,N,S.

후처리

  1. washwashed well with water
  2. customto give the crude dimesylate (Id: X=OSO2Me, R=SO2NH2)
  3. customwas removed under reduced pressure
  4. customThe residue was partitioned between EtOAc and water
  5. customchromatographed on silica gel
  6. washElution with EtOAc

출처 및 근거

ORD 기록
ord-58e099cbe67b4c2babec4188316728f8
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05571845

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