2-Propanol, reaction products with ammonia, distn. residues → 5-(3-chlorophenyl)-alpha-(4-chlorophenyl)-alpha-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine

HRID 347006ノート

反応式

HRID 347006 の反応式
[NH3:1].CC(O)C.Cl[C:7]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)([C:28]1[N:32]([CH3:33])[C:31]([S:34][CH3:35])=[N:30][N:29]=1)[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]1[N:18]=[N:19][N:20]=[C:13]1[N:12]=[C:11]2[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1>C1COCC1>[Cl:27][C:23]1[CH:22]=[C:21]([C:11]2[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([C:7]([C:36]4[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=4)([C:28]4[N:32]([CH3:33])[C:31]([S:34][CH3:35])=[N:30][N:29]=4)[NH2:1])[CH:9]=3)[N:14]3[N:18]=[N:19][N:20]=[C:13]3[N:12]=2)[CH:26]=[CH:25][CH:24]=1

参加物

4

反応物 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 210820857-[chloro(4-chlorophenyl)[4-methyl-5-(methylthio)-4H-1,2,4triazol-3-yl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a)quinazoline

生成物 1

HCID 210820625-(3-chlorophenyl)-alpha-(4-chlorophenyl)-alpha-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine収率 18%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

NH3/iPrOH saturated solution (40 ml) was added dropwise at 0° C. to a solution of 7-[chloro(4-chlorophenyl)[4-methyl-5-(methylthio)-4H-1,2,4triazol-3-yl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a)quinazoline (0.0036 mol) in THF (80 ml). The mixture was stirred from 0° C. to room temperature then at room temperature for 2 hours, poured out into ice water and extracted with EtOAc. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue (2 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 98/2/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.35 g (18%) of 5-(3-chlorophenyl)-α-(4-chlorophenyl)-α-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]-tetrazolo[1,5-a]quinazoline-7-methanamine. A sample (0.15 g) was crystallized from CH3CN/diethyl ether. The precipitate was filtered off and dried, yielding 0.05 g of 5-(3-chlorophenyl)-α-(4-chlorophenyl)-α-[4methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]-tetrazolo[1,5-a]quinazoline-7-methanamine, mp. 150° C.

後処理

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue (2 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 98/2/0.1; 15–40 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-728695abbde64105847111e3aa0210e3
出典データセット
uspto-grants-2007_02
特許番号
US07173040B2

反応ノート

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