Diethyl Ether → 1-(7-Oxo-4,5,6,7-tetrahydro-2-benzothiazolyl)-3-ethyl-urea

HRID 9106

反応式

HRID 9106 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[CH2:19]([N:21]=[C:22]=[O:23])[CH3:20].CCOCC>CN(C=O)C>[O:11]=[C:10]1[C:4]2[S:3][C:2]([NH:1][C:22]([NH:21][CH2:19][CH3:20])=[O:23])=[N:6][C:5]=2[CH2:7][CH2:8][CH2:9]1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 5878502-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one

生成物 1

HCID 219855571-(7-Oxo-4,5,6,7-tetrahydro-2-benzothiazolyl)-3-ethyl-urea収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A solution of 2-amino-7-oxo-4,5,6,7-tetrahydro-benzothiazole 3 (11.56 g, 68.7 mmol) in anhydrous DMF (200 mL) was treated with triethylamine (19.2 mL, 137 mmol, 2.0 eq) and ethyl isocyanate (10.9 nL, 137 mmol, 2.0 eq). The reaction mixture was heated at about 90° C. with stirring for about 3 hours. The DMF solvent was distilled off under reduced pressure. A sticky brown residue was obtained. Treatment with Et2O (100 mL) gave a precipitate, which was filtered off and washed with more Et2O (50 mL). The light brown colored solid was dried under vacuum to give 13.97 g (85%) of 4. The material was used in the following synthesis without further purification. 1H NMR (DMSO) δ 10.95 (br s, 1H, NH), 6.66 (br s, 1H, NH), 3.16 (p, 2H, J=7.2 Hz, CH2), 2.79 (t, 2H, J=6.1 Hz, CH2), 2.45 (t, 2H, J=6.5 Hz, CH2), 2.05 (p, 2H, J=6.4 Hz, CH2), 1.07 (t, 3H, J=7.2 Hz, CH3); LC/MS 240 (MH+); RP-HPLC RT 2.27 minutes.

後処理

  1. distillationThe DMF solvent was distilled off under reduced pressure
  2. customA sticky brown residue was obtained
  3. filtrationwas filtered off
  4. washwashed with more Et2O (50 mL)
  5. customThe light brown colored solid was dried under vacuum

出典と根拠

ORDレコード
ord-0f07a300f177487084962573f64fed09
出典データセット
uspto-grants-2006_08
特許番号
US07091227B2

関連ノート

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