Sulfuric Acid → Methyl 3-thioureidobenzoate

HRID 844594

Reaction equation

HRID 844594 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].S(=O)(=O)(O)O.[S-:17][C:18]#[N:19].[Na+].C1OCCOCCOCCOCCOC1>ClC1C=CC=CC=1>[NH:1]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:18]([NH2:19])=[S:17]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3633615-Crown-5HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 516871Sodium thiocyanate

Product 1

HCID 726316Methyl 3-thioureidobenzoateYield 85.9%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

11.3 g of methyl 3-aminobenzoate are initially introduced into the reaction vessel as a solution in 75 ml of chlorobenzene, 2.07 ml of concentrated sulfuric acid (96%) are added dropwise at −5 to 0° C. in the course of 15 minutes, stirring is continued for 5 minutes, 6.8 g of sodium thiocyanate are then introduced in portions at a maximum of 0° C. and the mixture is stirred for a further 15 minutes. 0.2 ml of 15-crown-5 is then added, the mixture is stirred at a bath temperature of 100° C. for 10 hours and cooled and the precipitate formed is filtered off and washed 3 times with water. 13.5 g (85.9%) of the title compound of melting point 171-172° C. result.

Workup

  1. stirringthe mixture is stirred for a further 15 minutes
  2. stirringthe mixture is stirred at a bath temperature of 100° C. for 10 hours
  3. temperaturecooled
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. washwashed 3 times with water

Sources & evidence

ORD record
ord-421a82e644a6485f863ca5c5672b39fa
Source dataset
uspto-grants-2002_04
Patent number
US06380422B1

Linked notes

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