Formaldehyde → 1-Ethyl-5-methyl-3-(6-nitro-1,3-benzothiazol-2-yl)-1,3,5-triazinan-2-one

HRID 9105

반응식

HRID 9105 반응식
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].C=O.CN.[CH3:23][N:24]1[CH2:29]COC[CH2:25]1>CO.CCO.O>[CH2:1]([N:3]1[CH2:25][N:24]([CH3:29])[CH2:23][N:6]([C:7]2[S:8][C:9]3[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[C:4]1=[O:5])[CH3:2]

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 79724-MethylmorpholineHCID 9813955N-Ethyl-N'-(6-nitro-1,3-benzothiazol-2-yl)urea

생성물 1

HCID 219855321-Ethyl-5-methyl-3-(6-nitro-1,3-benzothiazol-2-yl)-1,3,5-triazinan-2-one

시약·촉매·용매 2

HCID 887Methanol용매HCID 19096565Water ethanol용매

반응 조건

온도
80 °C

실험 절차

N-Ethyl-N′-(6-nitro-1,3-benzothiazol-2-yl)urea (2.8 g) was suspended in about 100 mL 1:1 EtOH/H2O at room temperature. About 8 mL of a 37% aqueous solution of formaldehyde is added followed by addition of about 15 mL of a 2M solution of MeNH2 in MeOH, then about 2.2 mL of N-methylmorpholine. The solution was warmed to about 80° C. then allowed to stir for about 16 hours. The slurry was then cooled to room temperature, filtered and washed well with water. After drying in vacuo, about 3.2 grams was isolated. 1H NMR 1.13 (t, 3H, J=7.1 Hz), 2.55 (s, 3H), 3.38 (q, 2H, J=7.1 Hz), 4.39 (s, 2H), 5.16 (s, 2H), 7.81 (d, 1H, J=8.9 Hz), 8.22 (dd, 1H, J=2.4 Hz, J=8.9 Hz), 8.95 (d, 1H, J=2.4 Hz) LC/MS=3.33 min, 322 (MH+), 320(M−H−).

후처리

  1. temperatureThe slurry was then cooled to room temperature
  2. filtrationfiltered
  3. washwashed well with water
  4. customAfter drying in vacuo
  5. customabout 3.2 grams was isolated
  6. custom1H NMR 1.13 (t, 3H, J=7.1 Hz), 2.55 (s, 3H), 3.38 (q, 2H, J=7.1 Hz), 4.39 (s, 2H), 5.16 (s, 2H), 7.81 (d, 1H, J=8.9 Hz), 8.22 (dd, 1H, J=2.4 Hz, J=8.9 Hz), 8.95 (d, 1H, J=2.4 Hz) LC/MS=3.33 min, 322 (MH+), 320(M−H−)

출처 및 근거

ORD 기록
ord-3d6f07f08bd342b498abd6f7a943c2cb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

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