Thiophosgene → HCID 68940748、化合物

HRID 1594508

反応式

HRID 1594508 の反応式
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:12]CN(C(C)C)C(C)C.C(Cl)(Cl)=S.[CH3:25][NH:26][C:27]1[C:28]([NH2:37])=[CH:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=1>C(Cl)Cl.[Cl-].[Na+].O.[Hg](OC(C(F)(F)F)=O)OC(C(F)(F)F)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:25]2[N:26]([CH3:12])[C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:29][C:28]=3[N:37]=2)=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 4

HCID 10040ThiophosgeneHCID 698614-Tert-ButylanilineHCID 81531Diisopropylethylamine2 回HCID 715666N1-Methyl-4-(trifluoromethyl)benzene-1,2-diamine

生成物 1

HCID 68940748HCID 68940748、化合物

試薬・触媒・溶媒 3

HCID 16685285Hg(TFA)2触媒HCID 6344Dichloromethane溶媒2 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
40 °C

実験手順

To a stirring solution of 4-t-butylaniline (1.3 mmol, 189 mg) and DIEA (2.53 mmol, 441 μL) in DCM (3 mL) at 0° C. was added dropwise thiophosgene (1.3 mmol, 91 μL). After 10 min the title compound of Example 6, Step B (10.5 mmol, 1.86 g) was added, and the reaction mixture was brought to 40° C. for 2 h. Hg(O2CCF3)2 (2.5 mmol, 1 g) and DIEA (1.3 mmol, 220 μL) were added and the reaction was heated at 40° C. for 16 h. The reaction was poured into DCM and brine containing Na2S, and the resulting slurry was filtered through celite. The organic phase was collected and dried over MgSO4 and concentrated in vacuo. Flash chromatography on silica eluting with 25% EtOAc in hexanes afforded the product as a yellow solid. LC-MS (ESI, Method B): 1.81 min, m/z 348.3 (M+1).

後処理

  1. additioncontaining Na2S
  2. filtrationthe resulting slurry was filtered through celite
  3. customThe organic phase was collected
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9e1d39459f8d4b19af4167a1ea9ef6c8
出典データセット
uspto-grants-2007_11
特許番号
US07301036B2

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