Hydrochloric Acid → 3-Isothiocyanato-4-methoxybenzoic acid

HRID 385183

반응식

HRID 385183 반응식
[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]

참가 물질

11

반응물 7

HCID 313Hydrochloric AcidHCID 807IodineHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 178233-Amino-4-methoxybenzoic acidHCID 24437Sodium Sulfite2회HCID 516892Sodium Bicarbonate

생성물 1

HCID 442063063-Isothiocyanato-4-methoxybenzoic acid수율 94%

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-16fb188c3b9b4fe390f9e99aa88604e7
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367857B2

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