4-Methylmorpholine → HCID 59652711, compound

HRID 1662836Notes

Reaction equation

HRID 1662836 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.CN1CCOCC1.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([Cl:31])=[C:26]([CH:30]=1)[C:27]([OH:29])=[O:28].C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:12][C:2]([F:1])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([Cl:31])=[C:26]([CH:30]=2)[C:27]([OH:29])=[O:28])=[O:9])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 99664-(Trifluoromethyl)benzoic acidHCID 378795-Amino-2-chlorobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 59652711HCID 59652711, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(trifluoromethyl)benzoic acid (1.0 g, 5.3 mmol) in DCM (20 mL) were added CDMT (1.1 g, 6.3 mmol) and NMM (2.3 mL, 21 mmol). The mixture was stirred at RT for 30 min under an argon atmosphere. 5-amino-2-chlorobenzoic acid (1.4 g, 7.9 mmol) was added and the mixture stirred at RT for additional 2 h. The reaction mixture was poured into saturated NaHCO3 solution and then extracted with DCM. The organic layer was dried (Na2SO4), filtered and the filtrate concentrated to afford the title compound (1.6 g, 88%) as a cream solid.

Workup

  1. stirringthe mixture stirred at RT for additional 2 h
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d6a2537f9ca9471184e4d40115697c8f
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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