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

HRID 9105

反応式

HRID 9105 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 19096565Water ethanol溶媒

反応条件

温度
80 °C

実験手順

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−).

後処理

  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−)

出典と根拠

ORDレコード
ord-3d6f07f08bd342b498abd6f7a943c2cb
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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