3-Chloroaniline → HCID 9878858, compound

HRID 896074Notes

Reaction equation

HRID 896074 reaction equation
ClC[NH:3][C:4]1[N:9]=[C:8]([S:10][CH3:11])[N:7]=[CH:6][N:5]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].[CH:20](N(CC)C(C)C)(C)C>O1CCCC1>[Cl:12][C:13]1[CH:14]=[C:15]([NH:16][CH2:20][C:6]2[N:7]=[C:8]([S:10][CH3:11])[N:9]=[C:4]([NH2:3])[N:5]=2)[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 81531DiisopropylethylamineHCID 69986299HCID 69986299, compound

Product 1

HCID 9878858HCID 9878858, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-(chloromethyl-4-methylthio-1,3,5-triazine-2-ylamine (75 mg, 0.39 mmol) in dry tetrahydrofuran (3 mL) was added a solution of 3-chloroaniline (0.210 mL, 1.97 mmol) in dry tetrahydrofuran (1 mL) followed by anhydrous N,N-diisopropylethylamine (0.343 mL, 1.95 mmol). The mixture was heated under reflux for 16 hours, after which the solvent was evaporated. The residue was purified by reverse phase HPLC to give 4-[(3-chlorophenylamino)methyl]-6-methylthio-[1,3,5]triazin-2-ylamine. M+1=266.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customafter which the solvent was evaporated
  4. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-b86f4d9923e3453ba39e4254d74339db
Source dataset
uspto-grants-2005_07
Patent number
US06919339B2

Reaction notes

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