Water → N-(5-Carboxymethyl-pentyl)-2,4-dichloro-3-cyano aniline
Reaction equation
[Cl:1][C:2]1[C:8]([C:9]#[N:10])=[C:7]([Cl:11])[CH:6]=[CH:5][C:3]=1[NH2:4].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2N=N1.C(N(CC)CC)C.[OH2:46].CN([CH:50]=[O:51])C>>[C:50]([CH2:22][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][NH:4][C:3]1[CH:5]=[CH:6][C:7]([Cl:11])=[C:8]([C:9]#[N:10])[C:2]=1[Cl:1])([OH:51])=[O:46]Participants
Procedure
2,4-Dichloro-3-cyano aniline (6.0 g, 32.1 mmol), hexanoic diacid (9.5 mL, 138.3 mmol), BOP (28.4 g, 64.2 mmol, Isochem) and triethyl amine (27.0 mL, 192.6 mmol) was dissolved in 75 mL DMF. The reaction was allowed to stand for 2 days at room temperature. TLC showed an insufficient reaction and a new portion of BOP, hexanoic diacid and triethyl amine was added. The reaction was stirred for a day at room temperature. Water (750 mL) was added to the reaction. The crude mixture was extracted by dichloromethane (400 mL). The dichloromethane was extracted with sodium carbonate (10%, 3 times) and hydrochloric acid (6M, 3 times). The dichloromethane was dried with magnesium sulfate and the resulting solution was concentrated in vacuum to yield a crude oily product (6.0 g, 60%) which was used directly without further purification in the next step.
Workup
- customan insufficient reaction
- extractionThe crude mixture was extracted by dichloromethane (400 mL)
- extractionThe dichloromethane was extracted with sodium carbonate (10%, 3 times) and hydrochloric acid (6M, 3 times)
- dry with materialThe dichloromethane was dried with magnesium sulfate
- concentrationthe resulting solution was concentrated in vacuum
Sources & evidence
- ORD record
- ord-1cb2b44515f146dc87531bbb04cc61e8
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06635434B1
Reaction notes
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