Thionyl Chloride → 3-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoyl chloride

HRID 1249139노트

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HRID 1249139 반응식
COC(=O)[C@H](CC1C=C(I)C(OC2C=C(I)C(O)=C(I)C=2)=C(I)C=1)N[C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]2=[O:19])[CH:8]=1.C1(=O)N(C2C=C(C=CC=2)C(O)=O)C(=O)C=C1.S(Cl)([Cl:59])=O>>[C:17]1(=[O:18])[N:13]([C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[C:6]([Cl:59])=[O:20])[C:14](=[O:19])[CH:15]=[CH:16]1

참가 물질

4

반응물 3

HCID 24386Thionyl ChlorideHCID 869263-(2,5-Dihydro-2,5-dioxo(1H)-pyrrole-1-yl)benzoic acidHCID 22819792HCID 22819792, 화합물

생성물 1

HCID 30172973-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoyl chloride

실험 절차

Preparation of m-maleimidobenzoyl thyroxine methyl ester (as described by Monji, N., Malkus, H, and Castro, A., Biochem. Biophys. Res. Commun., 1978, 85, 671-677). m-Maleimidobenzoic acid (225 mg, 1.06 mmol) was dissolved in 4 mL of thionyl chloride and refluxed for 30 minutes. Removal of excess thionyl chloride under reduced pressure afforded m-maleimidobenzoyl chloride as a pale yellow solid. The acid chloride (220 mg dissolved in 10 mL of tetrahydrofuran) was added dropwise to a stirred suspension of 400 mg (0.51 mmol) of thyroxine methyl ester and 400 mg of sodium carbonate. After the addition was complete, the mixture was refluxed for 30 minutes. Removal of the solvent under reduced pressure yielded a crude yellow product. The material was purified by silica gel chromatography with chloroform as the eluent. 1NMR (CDCl3) δ 3.85 (3 H,s), 3.92 (1 H,m), 5.77 (1 H,s), 6.90 (2 H,s), 7.12 (2 H,s), 7.57 (2 H,m), 7.70 (2 H,s), 7.80 (2 H,m). Anal. calcd. for C27H18I4N2O7 : C, 32.8; H, 1.82; N, 2.80. Found: C, 32.7; H, 2.09; N, 2.42.

후처리

  1. temperaturerefluxed for 30 minutes
  2. customRemoval of excess thionyl chloride under reduced pressure

출처 및 근거

ORD 기록
ord-6fb0d21df9894bf192538360d65058bf
출처 데이터셋
uspto-grants-1986_12
특허 번호
US04629689

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