Methanol → 1-(6-Bromo-7-benzyloxy-2-benzothiazolyl)-3-ethyl-urea

HRID 9112ノート

反応式

HRID 9112 の反応式
[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1[OH:17].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CO>CN(C=O)C>[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1[O:17][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

6

反応物 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 219855951-(6-Bromo-7-hydroxy-2-benzothiazolyl)-3-ethylurea

生成物 1

HCID 219856041-(6-Bromo-7-benzyloxy-2-benzothiazolyl)-3-ethyl-urea収率 45%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
20 °C

実験手順

A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6 (0.050 g, 0.16 mmol) and potassium carbonate (0.023 g, 0.17 mmol, 1.05 eq) in anhydrous DMF (1.6 mL) was stirred at about 20° C. for about 0.5 hour, and was cooled down to about 0° C. The reaction mixture was treated with benzyl bromide (0.019 mL, 0.16 mmol, 1.0 eq), and was stirred at about 0° C. for about 16 hours. To the reaction mixture was added methanol (10 mL). The solid was filtered off and rinsed with methanol (3 mL). The solvent was evaporated and the residue was dissolved in DMF (2 mL). The crude reaction solution was purified by LC/MS to give 0.029 g (45%) of the desired compound 9. 1H NMR (DMSO) δ 10.86 (br s, 1H, NH), 7.59–7.34 (m, 7H, ArH), 6.72 (br s, 1H, NH), 5.17 (s, 2H, CH2), 3.18 (m, 2H, CH2), 1.09 (t, 3H, J=7.2 Hz, CH3); LC/MS 406 (MH+); RP-HPLC RT 3.8 minutes.

後処理

  1. temperaturewas cooled down to about 0° C
  2. stirringwas stirred at about 0° C. for about 16 hours
  3. filtrationThe solid was filtered off
  4. washrinsed with methanol (3 mL)
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in DMF (2 mL)
  7. customThe crude reaction solution
  8. customwas purified by LC/MS

出典と根拠

ORDレコード
ord-c5baa1466eb64f28875bdeda9757c685
出典データセット
uspto-grants-2006_08
特許番号
US07091227B2

反応ノート

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