Sulfuric Acid → Methyl 3-thioureidobenzoate

HRID 560311

Reaktionsgleichung

Reaktionsgleichung von HRID 560311
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11].[C:17]([S-:19])#[N:18].[K+].C1OCCOCCOCCOCCOCCOC1>ClC1C=CC=CC=1>[CH3:13][O:12][C:10](=[O:11])[C:9]1[CH:14]=[CH:15][CH:16]=[C:7]([NH:6][C:17]([NH2:18])=[S:19])[CH:8]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 2855718-Crown-6HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 516872Potassium thiocyanate

Produkt 1

HCID 726316Methyl 3-thioureidobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

At −10° C. sulfuric acid (0.46 mL) is added dropwise to a solution of methyl 3-aminobenzoate (17.2 mmol) in chlorobenzene (19 mL). After 15 min KSCN (18.2 mmol) is added portionwise over 30 min. The mixture is treated with 18-crown-6, heated to 100° C. for 16 h and allowed to cool to RT. After 4 h the obtained precipitate is filtered off and washed successively with chlorobenzene (33 mL) and hexane (three times 130 mL). The residue is diluted with water (390 mL) and the suspension is stirred for 30 min. After filtration the residue is washed twice with water (130 ml, each), concentrated in vacuo and dried additionally by azeotropic removal of water with toluene. The obtained product is used without further purification.

Aufarbeitung

  1. temperatureto cool to RT
  2. filtrationAfter 4 h the obtained precipitate is filtered off
  3. washwashed successively with chlorobenzene (33 mL) and hexane (three times 130 mL)
  4. additionThe residue is diluted with water (390 mL)
  5. filtrationAfter filtration the residue
  6. washis washed twice with water (130 ml
  7. concentrationeach), concentrated in vacuo
  8. dry with materialdried additionally by azeotropic removal of water with toluene
  9. customThe obtained product is used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-a20c4954878f43a98813a566117f52bc
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063099B2

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