Sodium Hydroxide → 1-Amino-2-naphthalenethiol

HRID 1382709

反応式

HRID 1382709 の反応式
[OH-].[Na+].[N:3]1[C:7]2[C:8]3[C:13]([CH:14]=[CH:15][C:6]=2[S:5]C=1N)=[CH:12][CH:11]=[CH:10][CH:9]=3>O.C(O)CO>[NH2:3][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[SH:5]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 94880Naphtho[1,2-d]thiazol-2-amine

生成物 1

HCID 1133141-Amino-2-naphthalenethiol収率 67.3%

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 962Water溶媒2 回

実験手順

To a solution of 30.0 g sodium hydroxide in 30 ml of water and 180 ml of ethylene glycol was added 18.0 g (0.089 mol) of naphtho[1,2-d]thiazol-2-amine. The mixture was stirred and heated at reflux under nitrogen for 20 hours then diluted with 100 ml of water. After cooling to room temperature the mixture was extracted with ether (4×95 ml). The aqueous solution was cooled in an ice-bath and neutralized with acetic acid. The aqueous suspension was extracted with ether (3×175 ml). The combined ether solutions were washed with water and dried (MgSO4). Removal of the solvent gave a residue to which heptane (3×50 ml) was added and distilled off under reduced pressure to give 10.5 g (67%) of 1-aminonaphthalene-2-thiol. This compound is sensitive to air, and therefore was used immediately for the condensation with the glycidate. For analysis a sample of this compound was distilled at 110°-115° (0.05 mm), mp 36°-37°.

後処理

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 20 hours
  3. extractionwas extracted with ether (4×95 ml)
  4. temperatureThe aqueous solution was cooled in an ice-bath
  5. extractionThe aqueous suspension was extracted with ether (3×175 ml)
  6. washThe combined ether solutions were washed with water
  7. dry with materialdried (MgSO4)
  8. customRemoval of the solvent
  9. customgave a residue to which heptane (3×50 ml)
  10. additionwas added
  11. distillationdistilled off under reduced pressure

出典と根拠

ORDレコード
ord-982e19eccf5e444992fd8e1786d07ca2
出典データセット
uspto-grants-1989_02
特許番号
US04808580

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