Ammonia → 3,5-Dichloro-2-hydroxybenzenesulfonamide

HRID 2295463ノート

反応式

HRID 2295463 の反応式
[Cl:1][C:2]1[C:3]([OH:13])=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH3:14]>O1CCCC1>[Cl:1][C:2]1[C:3]([OH:13])=[C:4]([S:9]([NH2:14])(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

4

反応物 2

HCID 222AmmoniaHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chloride

生成物 1

HCID 2947193,5-Dichloro-2-hydroxybenzenesulfonamide収率 97.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 26.1 gm (0.1 mole) 3,5-dichloro-2-hydroxybenzenesulfonyl chloride in 400 ml dry tetrahydrofuran was cooled to 0° with an ice bath, and 11 ml (0.5 mole) anhydrous ammonia was added dropwise, with stirring. The rate of addition was sufficiently slow so as to keep the temperature of the reaction medium less than 10°. The mixture was stirred for 1.5 hours at 0° then slowly warmed to room temperature. The solvent was removed in vacuo and the residue was treated with 100 ml H2O. A small amount of insoluble by-product was filtered off and then the aqueous solution was acidified to pH=2.0 with 1 N HCl solution. Filtration of the resulting white precipitate and drying of the precipitate at 50° under vacuum gave 23.6 gm (97%) white solid, m.p. >225°. The infrared spectrum showed strong absorption at 3300, 1540, 1450 and 1320 cm-1, and the nuclear magnetic resonance spectrum showed a broad singlet at 7.2δ, 3 protons, and a doublet of doublets at 7.8δ, 2 protons. These data are consistent with the desired product.

後処理

  1. additionThe rate of addition
  2. customthe temperature of the reaction medium less than 10°
  3. stirringThe mixture was stirred for 1.5 hours at 0°
  4. customThe solvent was removed in vacuo
  5. additionthe residue was treated with 100 ml H2O
  6. filtrationA small amount of insoluble by-product was filtered off
  7. filtrationFiltration of the resulting white precipitate
  8. customdrying of the precipitate at 50° under vacuum

出典と根拠

ORDレコード
ord-feb42b22df4a41b7b36dcda026e9dfd1
出典データセット
uspto-grants-1984_01
特許番号
US04425153

反応ノート

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