5-Amino-2-chlorobenzoic acid → 2-Chloro-5-[(thiophene-2-carbonyl)amino]-benzoic acid

HRID 1662813Notes

Reaction equation

HRID 1662813 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].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](Cl)=[O:18]>C1COCC1>[Cl:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:17]([C:13]2[S:12][CH:16]=[CH:15][CH:14]=2)=[O:18])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 378795-Amino-2-chlorobenzoic acidHCID 789282-Thiophenecarbonyl chloride

Product 1

HCID 242143502-Chloro-5-[(thiophene-2-carbonyl)amino]-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-2-chloro-benzoic acid (0.349 g, 2.03 mmol) was diluted with THF (12 mL), treated with thiophene-2-carbonyl chloride (0.240 mL, 2.23 mmol) and stirred overnight. Solvents were then removed and resulting solids were triturated with DCM. After filtration, the title compound was obtained as a white solid (0.5 g, 88%).

Workup

  1. customSolvents were then removed
  2. customresulting solids
  3. customwere triturated with DCM
  4. filtrationAfter filtration

Sources & evidence

ORD record
ord-25c6b2b9ced347c2966eaa12d189ae16
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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