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Dichloromethane → 3-Benzylamino-4-[3-(3-piperidinomethylphenoxy)propylamino]-1,2,5-thiadiazole

HRID 483250
ノート
印刷プレビュー

反応式

HRID 483250 の反応式
Cl.Cl.Cl.[CH2:4]([NH:11][C:12](=[NH:33])[C:13](=[NH:32])[NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:20]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(Cl)Cl.[S:37](N1C(=O)C2=CC=CC=C2C1=O)N1C(=O)C2=CC=CC=C2C1=O>C(N(CC)CC)C>[CH2:4]([NH:11][C:12]1[C:13]([NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:20]=2)=[N:32][S:37][N:33]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 821962,2'-Thiobis(1H-isoindole-1,3(2H)-dione)HCID 178478597HCID 178478597、化合物

生成物 1

HCID 133136883-Benzylamino-4-[3-(3-piperidinomethylphenoxy)propylamino]-1,2,5-thiadiazole収率 77.3%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

A mixture of N-benzyl-N'-[3-(3-piperidinomethylphenoxy)propyl]ethanediimidamide trihydrochloride (4.73 g; 9.16 mmoles) [prepared in Step A], 45 ml of CH2Cl2 and 3.8 ml of triethylamine was treated with N,N'-thiobisphthalimide (DMF solvate) (3.64 g; 9.16 mmoles) and stirred for one hour. The mixture was washed with 44 ml of 10% KOH, dried (MgSO4), filtered, diluted with toluene and concentrated. The residue was chromatographed by flash chromatography on 110 g of silica gel (230-400 mesh) using ethyl acetate as the eluent to give 3.1 g (77%) of the title compound. Treatment of the product with an equivalent amount of aqueous HCl in 2-propanol gave the hydrochloride salt of the title compound, mp 138°-141° C. Anal. Calc'd. for C24H31N5OS.HCl: C, 60.80; H, 6.80; N, 14.77; S, 6.76; Cl, 7.48; Found: C, 60.53; H, 6.64; N, 14.99; S, 6.91; Cl, 7.47.

後処理

  1. washThe mixture was washed with 44 ml of 10% KOH
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. additiondiluted with toluene
  5. concentrationconcentrated
  6. customThe residue was chromatographed by flash chromatography on 110 g of silica gel (230-400 mesh)

出典と根拠

ORDレコード
ord-027d7ce3a6464f30ab2124bc0f075fa9
出典データセット
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04578471

反応ノート

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