Ammonia → HCID 15521569、化合物

HRID 413027ノート

反応式

HRID 413027 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:9]2[CH2:12][CH:11]([NH2:13])[CH2:10]2)=[CH:4][CH:3]=1.[C:21]1([S:31](Cl)(=[O:33])=[O:32])[CH:26]=[CH:25][CH:24]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:22]=1.C([N:37](CC)CC)C.N>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:9]2[CH2:10][CH:11]([NH:13][S:31]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([S:27](=[O:29])(=[O:28])[NH2:37])[CH:22]=3)(=[O:33])=[O:32])[CH2:12]2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 962401,3-Benzenedisulfonyl dichlorideHCID 218965981-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamine

生成物 1

HCID 15521569HCID 15521569、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 0.307 g of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine is added dropwise, at room temperature, to a solution of 0.412 g of 1,3-benzenedisulfonic acid dichloride and 0.165 cm3 of triethylamine in 10 cm3 of acetonitrile. After stirring for 3 hours at room temperature, 0.28 cm3 of a 20% solution of ammonia is added and the reaction mixture is left at room temperature. After 18 hours, the mixture is filtered and concentrated to dryness under reduced pressure (2.7 kPa). After chromatography on a silica gel column (particle size 0.06-0.200 mm, height 35 cm, diameter 2 cm), eluting under an argon pressure of 0.9 bar with dichloromethane and then a mixture of dichloromethane+1% methanol and then a mixture of dichloromethane+2% methanol by volume and collecting 30-cm3 fractions, fractions 23 to 34 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give 90 mg of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-3-sulfamoylphenylsulfonamide in the form of a white solid [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 2.78 (broad t, J=7 Hz: 2H); 3.35 (broad t, J=7 Hz: 2H); 4.01 (mt: 1H); 4.24 (s: 1H); 5.27 (unresolved complex: 2H); 5.61 (unresolved complex: 1H); from 7.15 to 7.35 (mt: 8H); 7.67 (t, J=8 Hz: 1H); 8.04 (broad d, J=8 Hz: 1H); 8.12 (broad d, J=8 Hz: 1H); 8.49 (broad s: 1H)].

後処理

  1. waitthe reaction mixture is left at room temperature
  2. waitAfter 18 hours
  3. filtrationthe mixture is filtered
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. washAfter chromatography on a silica gel column (particle size 0.06-0.200 mm, height 35 cm, diameter 2 cm), eluting under an argon pressure of 0.9 bar with dichloromethane
  6. additiona mixture of dichloromethane+1% methanol
  7. additiona mixture of dichloromethane+2% methanol by volume
  8. customcollecting 30-cm3 fractions, fractions 23 to 34
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

出典と根拠

ORDレコード
ord-ef90b727c5ff4e28b6f093239afb5780
出典データセット
uspto-grants-2003_05
特許番号
US06566356B2

反応ノート

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