2-Amino-5-fluorobenzoic acid → HCID 12088011, compound

HRID 897047Notes

Reaction equation

HRID 897047 reaction equation
[F:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([NH2:11])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]=[C:20]=[S:21]>C(O)(=O)C.C(OCC)(=O)C.CCOCC>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[C:7](=[O:9])[C:6]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=2)[NH:11][C:20]1=[S:21]

Participants

6

Reactant 2

HCID 1014122-Amino-5-fluorobenzoic acidHCID 1231711-Chloro-2-isothiocyanatobenzene

Product 1

HCID 12088011HCID 12088011, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.04 g (6.71 mmol) of 5-fluoroanthranilic acid and 1.13 g (6.71 mmol) of 2-chlorophenylisothiocyanate in 10 ml of glacial acetic acid was refluxed for 2.5 hours. The reaction mixture was cooled and the acetic acid was evaporated to give a yellow solid residue, which was taken up in ethyl acetate and ether. The solid was filtered off and washed with ether and air dried to give 1.48 g (72%) of the desired product, m.p. 295-297° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe acetic acid was evaporated
  3. customto give a yellow solid residue, which
  4. filtrationThe solid was filtered off
  5. washwashed with ether and air
  6. customdried

Sources & evidence

ORD record
ord-5f29155e9eea4e3796e25f0cdaa8a772
Source dataset
uspto-grants-2005_07
Patent number
US06921764B2

Reaction notes

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