Tetrahydrofuran → HCID 86664616, compound

HRID 537159Notes

Reaction equation

HRID 537159 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH2:11])[C:5]([OH:7])=[O:6].[N:12]([CH3:15])=[C:13]=[S:14].O1CCC[CH2:17]1>>[NH2:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([O:7][CH3:17])=[O:6])=[CH:3][C:2]=1[NH:1][C:13]([NH:12][CH3:15])=[S:14]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11167Methyl isothiocyanateHCID 692633,4-Diaminobenzoic acid

Product 1

HCID 86664616HCID 86664616, compoundYield 56%

Procedure

A mixture of 3,4-diaminobenzoic acid (15 g, 0.09 mol) and isothiocyanatomethane (6.6 g, 0.09 mol) was dissolved in tetrahydrofuran (90 mL). The reaction was heated at reflux for 3 hours and was then concentrated. The residue was poured into ice water. The resulting precipitate was filtered, washed with water, and dried under vacuum to give methyl 4-amino-3-(3-methylthioureido)benzoate (12.0 g, 56%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 hours
  3. concentrationwas then concentrated
  4. additionThe residue was poured into ice water
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-2de588cec4cd494cabd6c777f23bb0ff
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

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