3-(Trifluoromethyl)phenyl isocyanate → HCID 59652743, compound

HRID 1662831Notes

Reaction equation

HRID 1662831 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]=[C:21]=[O:22])[CH:15]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:21]([NH:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:23])[F:24])[CH:15]=2)=[O:22])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 378795-Amino-2-chlorobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 59652743HCID 59652743, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2-chlorobenzoic acid (0.86 g, 5 mmol) in anhydrous CH2Cl2 (40 mL) was added 1-(trifluoromethyl)-3-isocyanatobenzene (1.03 g, 5.5 mmol). The mixture was stirred overnight at room temperature. The saturated NaHCO3 (40 mL) was added and the mixture was stirred for 5 min. The organic layer was separated and aqueous was extracted with CH2Cl2 (3×20 mL). The combined organic solution was dried (Na2SO4). The solvent was removed in vacuo. The title compound was afforded as a white solid (1.68 g, 94%).

Workup

  1. stirringthe mixture was stirred for 5 min
  2. customThe organic layer was separated
  3. extractionaqueous was extracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe combined organic solution was dried (Na2SO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-44ce2e45aceb44f5aeb14119fdf465f0
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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