Sulfuric Acid → N-(2-Methyl-3-methoxycarbonylphenyl)thiourea

HRID 1263406Notes

Reaction equation

HRID 1263406 reaction equation
[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].S(=O)(=O)(O)O.[S-:18][C:19]#[N:20].[Na+].C1OCCOCCOCCOCCOC1>ClC1C=CC=CC=1>[CH3:12][C:3]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=1[NH:1][C:19]([NH2:20])=[S:18]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3633615-Crown-5HCID 516871Sodium thiocyanateHCID 38010253-Amino-2-methylbenzoic acid methyl ester

Product 1

HCID 18616039N-(2-Methyl-3-methoxycarbonylphenyl)thiourea

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

90.7 g of methyl 3-amino-2-methylbenzoate (0.55 mol) were dissolved in 510 ml of chlorobenzene and, at −5° C., admixed with 14 ml of conc. sulfuric acid and 49 g of sodium thiocyanate (0.6 mol). 2 ml of 15-crown-5 were then added, and the reaction mixture was heated at 100° C. for 13 h. After cooling, the solid was filtered off with.suction, washed with water and dried. Yield: 104.8 g (85%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered off with.suction,
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-06b0b366a69140308df118a7f6eb5f76
Source dataset
uspto-grants-2003_04
Patent number
US06541423B1

Reaction notes

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