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Methylamine → 4-Amino-2-chloro-5-[(methylamino)sulfonyl]benzenesulfonyl chloride

HRID 979772
ノート
印刷プレビュー

反応式

HRID 979772 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([Cl:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[S:13](Cl)(=[O:15])=[O:14].CN.[CH2:19]([N:21](CC)CC)C>O1CCCC1.C1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([Cl:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[S:13]([NH:21][CH3:19])(=[O:15])=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 695934-Amino-6-chlorobenzene-1,3-di(sulphonyl chloride)

生成物 1

HCID 137554674-Amino-2-chloro-5-[(methylamino)sulfonyl]benzenesulfonyl chloride

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Cool a solution of 4-amino-6-chloro-1,3-benzenedisulfonyl chloride (32.3 g) in tetrahydrofuran (THF, 150 ml) to -78° C. under a nitrogen atmosphere. Add a solution of 1.45 Molar methylamine in benzene (100 ml) containing triethylamine (10.1 g) dropwise with stirring over 45 minutes. After the addition is complete, stir at room temperature for 3 hours. Vacuum evaporate the solvent and partition the residue between ethyl acetate (EtOAc) (500 ml) and 10% aqueous citric acid (50 ml). Separate the organic layer and wash with saturated aqueous NaHCO3 (100 ml) followed by brine (100 ml). Dry the solution over Na2SO4, filter and vacuum evaporate the solvent. Triturate the residue with ether (100 ml) and collect the product by filtration. Vacuum dry at room temperature to give the title compound, m.p. 153°-155° C. Rf (silica gel; CH2Cl2 :EtOAc,97:3)=0.40.

後処理

  1. additionAfter the addition
  2. stirringstir at room temperature for 3 hours
  3. customVacuum evaporate the solvent
  4. custompartition the residue between ethyl acetate (EtOAc) (500 ml) and 10% aqueous citric acid (50 ml)
  5. customSeparate the organic layer
  6. washwash with saturated aqueous NaHCO3 (100 ml)
  7. dry with materialDry the solution over Na2SO4
  8. filtrationfilter
  9. customvacuum evaporate the solvent
  10. customTriturate the residue with ether (100 ml)
  11. customcollect the product
  12. filtrationby filtration
  13. customVacuum dry at room temperature

出典と根拠

ORDレコード
ord-135462b480d2424b8a833ed8ee27c2ef
出典データセット
uspto-grants-1987_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04634689

反応ノート

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