Hydrochloric Acid → 4-Carboxy-2-methylphenylisothiocyanate

HRID 385179

反応式

HRID 385179 の反応式
[C:1](=[S:3])=S.[NH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[CH3:14].C(N(CC)CC)C.II.Cl.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.O1CCCC1.O>[N:4]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[CH3:14])=[C:1]=[S:3]

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 24437Sodium SulfiteHCID 755984-Amino-3-methylbenzoic acid

生成物 1

HCID 390582644-Carboxy-2-methylphenylisothiocyanate収率 103%

試薬・触媒・溶媒 3

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

実験手順

Carbon disulfide (0.26 mL, 4.4 mmol) was added to a mixture comprising 4-amino-3-methylbenzoic acid (0.23 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 28 hours. The obtained reaction mixture was dropwise added to a tetrahydrofuran (1.0 mL) solution of iodine (0.41 g, 1.6 mmol) over a period of 5 minutes at 0° C., followed by stirring at 0° C. for further 1.5 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 residue, ethyl acetate (6 mL) and water (1 mL) were added, and the organic layer was washed once with 1M hydrochloric acid (1 mL) and then concentrated under reduced pressure to dryness to obtain 4-isothiocyanato-3-methylbenzoic acid as a cream-colored solid (0.30 g, yield: 103%, HPLC purity: 88%, HPLC retention time: 4.0 min). LC-MS ES-192 (retention time: 4.3 min, condition 1).

後処理

  1. customThe obtained reaction mixture
  2. stirringby stirring at 0° C. for further 1.5 hours
  3. additionmixed
  4. customthe organic layer was separated
  5. concentrationconcentrated under reduced pressure to dryness
  6. additionTo the residue, ethyl acetate (6 mL) and water (1 mL) were added
  7. washthe organic layer was washed once with 1M hydrochloric acid (1 mL)
  8. concentrationconcentrated under reduced pressure to dryness

出典と根拠

ORDレコード
ord-b9888b077d2a44e88b607df665d6b026
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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