Water → HCID 86725245, compound

HRID 576604Notes

Reaction equation

HRID 576604 reaction equation
[C:1](=[S:3])=S.[NH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH2:15][NH2:16])[C:8]([O:10][CH3:11])=[O:9].O>N1C=CC=CC=1>[S:3]=[C:1]1[NH:16][CH2:15][C:14]2[C:5](=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=2)[NH:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 6348Carbon DisulfideHCID 86725246HCID 86725246, compound

Product 1

HCID 86725245HCID 86725245, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Carbon disulfide (1.36 mL, 22.6 mmol) was added to a solution of methyl 3-amino-4-(aminomethyl)benzoate (2.0 g, 11.3 mmol) in pyridine (10 mL) and the resultant reaction mixture was stirred at 60° C. overnight. After cooling, water was added to the reaction mixture. The solid formed was filtrated to afford methyl 2-thioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (2.2 g) which was carried to the next step without further purification.

Workup

  1. customthe resultant reaction mixture
  2. temperatureAfter cooling
  3. customThe solid formed
  4. filtrationwas filtrated

Sources & evidence

ORD record
ord-6e52ed69d2124e588822a4e10e85ae71
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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