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1,2-Dichloro-4-isothiocyanatobenzene → HCID 178462557、化合物

HRID 603172
ノート
印刷プレビュー

反応式

HRID 603172 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=S)[CH:5]=[CH:6][C:7]=1[Cl:8].[N:12]#[C:13][NH2:14].[Na].Cl.CN(C)CCCN=C=NCC.[CH2:28]([N:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([CH2:36][N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH2:31]1)[CH3:29]>C(O)C.CN(C)C=O>[C:13]([N:14]=[C:10]([N:40]1[CH2:39][CH2:38][N:37]([CH2:36][C@@H:32]2[CH2:33][CH2:34][CH2:35][N:30]([CH2:28][CH3:29])[CH2:31]2)[CH2:42][CH2:41]1)[NH:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)#[N:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 230651,2-Dichloro-4-isothiocyanatobenzeneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57375518CyanamidnatriumHCID 576568471-{[(3R)-1-ethylpiperidin-3-yl]methyl}piperazine

生成物 1

HCID 178462557HCID 178462557、化合物収率 37.6%

試薬・触媒・溶媒 2

HCID 702
Ethanol
溶媒
HCID 6228Dimethylformamide溶媒

実験手順

3,4-Dichlorophenylisothiocyanate (204 mg) and sodium hydrogen cyanamide (70 mg) were refluxed in ethanol (20 ml) for three hours. The mixture was allowed to cool to room temperature then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (211 mg), 1-{[(3R)-1-ethylpiperidin-3-yl]methyl}piperazine (220 mg) and N,N-dimethylformamide (2 ml) were added and the reaction left to stir for 18 hours then concentrated in vacuo. The crude product was subjected to reverse phase HPLC using a gradient of 95% water/acetonitrile/0.1% TFA through to 50% water/acetonitrile/0.1% TFA. The combined product fractions were concentrated in vacuo then separated between dichloromethane (50 ml) and saturated sodium bicarbonate solution (100 ml). The dichloromethane layer was separated, dried over magnesium sulphate, filtered and concentrated in vacuo to give the title compound (159 mg).

後処理

  1. waitthe reaction left
  2. concentrationthen concentrated in vacuo
  3. concentrationThe combined product fractions were concentrated in vacuo
  4. customthen separated between dichloromethane (50 ml) and saturated sodium bicarbonate solution (100 ml)
  5. customThe dichloromethane layer was separated
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-90ddf7e1382a455c943958080b3133a0
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07906645B2

反応ノート

読み込み中…

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