Hydrochloric Acid → 3-Isothiocyanato-4-methoxybenzoic acid

HRID 385183

反応式

HRID 385183 の反応式
[C:1](=[S:3])=S.[NH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9].C(N(CC)CC)C.II.Cl.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.O1CCCC1>[N:4]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9])=[C:1]=[S:3]

参加物

11

反応物 7

HCID 313Hydrochloric AcidHCID 807IodineHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 178233-Amino-4-methoxybenzoic acidHCID 24437Sodium Sulfite2 回HCID 516892Sodium Bicarbonate

生成物 1

HCID 442063063-Isothiocyanato-4-methoxybenzoic acid収率 94%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒2 回

実験手順

Carbon disulfide (0.26 mL, 4.4 mmol) was added to a mixture comprising 3-amino-4-methoxybenzoic acid (0.25 g, 1.5 mmol), tetrahydrofuran (1.0 mL), water (1.0 mL) and triethylamine (0.51 mL, 3.6 mmol), followed by stirring at room temperature for 6 hours. To the obtained reaction mixture, a tetrahydrofuran (1.0 mL) solution of iodine (0.41 g, 1.6 mmol) was dropwise added over a period of 5 minutes at 0° C., followed by stirring at 0° C. for further 2.5 hours. Thereafter, 1M hydrochloric acid (1.5 mL) and sodium sulfite (38 mg, 0.30 mmol) were added and mixed. Then, ethyl acetate (6 mL) was added, and the organic layer was separated and concentrated under reduced pressure to dryness. To the obtained residue, ethyl acetate (6 mL), water (2 mL), sodium hydrogencarbonate (6 mg, 0.07 mmol) and sodium sulfite (9 mg, 0.07 mmol) were added, the organic layer was separated and concentrated under reduced pressure to dryness to obtain 3-isothiocyanato-4-methoxybenzoic acid as a colorless solid (0.29 g, yield: 94%, HPLC purity: 99%, HPLC retention time: 3.5 min). LC-MS ES-208 (retention time: 21.6 min, condition 3).

後処理

  1. customTo the obtained reaction mixture
  2. stirringby stirring at 0° C. for further 2.5 hours
  3. additionmixed
  4. customthe organic layer was separated
  5. concentrationconcentrated under reduced pressure to dryness
  6. customthe organic layer was separated
  7. concentrationconcentrated under reduced pressure to dryness

出典と根拠

ORDレコード
ord-16fb188c3b9b4fe390f9e99aa88604e7
出典データセット
uspto-grants-2013_02
特許番号
US08367857B2

関連ノート

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