Dimethylformamide → HCID 22496152, compound

HRID 1815896Notes

Reaction equation

HRID 1815896 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CN(C=O)C.CCN(C(C)C)C(C)C.[NH2:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31]([NH2:33])=[O:32])[CH:27]=[CH:28][CH:29]=1>CCOC(C)=O.O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:23][C:24]2[CH:25]=[C:26]([CH2:30][C:31]([NH2:33])=[O:32])[CH:27]=[CH:28][CH:29]=2)[N:7]=1

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 1088232-(3-aminophenyl)acetamide

Product 1

HCID 22496152HCID 22496152, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2,4-Dichloro-1,3,5-triazine (173.7 mg, 1.158 mmol) was dissolved into DMF (1 ml). To the stirring solution, cooled to 0° C., was added DIEA (202 μl , 1.158 mmol). This solution was added dropwise to a 0° C. mix of DMF (1 ml) and 3-aminophenyl acetamide. The reaction was stirred at 0° C. for 15 min and then at RT for 1 h. The reaction mix was diluted with EtOAc and water. The layers were separated, and the aqueous layer was extracted twice with EtOAc. The combined organic layer was washed 3 times with brine, dried over Na2SO4, and concentrated under reduced pressure, giving 2-[3-(4-chloro-[1,3,5]triazin-2-ylamino)-phenyl]acetamide.

Workup

  1. additionThis solution was added dropwise to a 0° C.
  2. waitat RT for 1 h
  3. additionThe reaction mix
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted twice with EtOAc
  6. washThe combined organic layer was washed 3 times with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0973cd48c14d4dd2b6685025ba6108d5
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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