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

HRID 1249139ノート

反応式

HRID 1249139 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6fb0d21df9894bf192538360d65058bf
出典データセット
uspto-grants-1986_12
特許番号
US04629689

反応ノート

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