Sulfuric Acid → Methyl 3-thioureidobenzoate

HRID 560311

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-a20c4954878f43a98813a566117f52bc
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063099B2

Linked notes

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