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

HRID 9106

반응식

HRID 9106 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0f07a300f177487084962573f64fed09
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

연결된 노트

불러오는 중…