2-Chloroethyl Isothiocyanate → 2-Chloro-4-(2-thiazolinylamino)benzoic acid methyl ester

HRID 1060488Notes

Reaction equation

HRID 1060488 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[Cl:11].Cl[CH2:14][CH2:15][N:16]=[C:17]=[S:18]>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:17]2[S:18][CH2:14][CH2:15][N:16]=2)=[CH:6][C:5]=1[Cl:11]

Participants

4

Reactant 2

HCID 1386612-Chloroethyl IsothiocyanateHCID 11839197Methyl 4-Amino-2-chlorobenzoate

Product 1

HCID 695646282-Chloro-4-(2-thiazolinylamino)benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-amino-2-chlorobenzoic acid methyl ester (0.5 g) and 2-chloroethylisothiocyanate (0.26 mL) in THF (20 mL) was refluxed for 24 h. THF was distilled and the residue was purified by column chromatography (silica gel: eluent: hexane/EtOAc 3:1-1:1) to yield 2-chloro-4-(2-thiazolinylamino)benzoic acid methyl ester (74 mg). ESMS: m/z 271 (MH+).

Workup

  1. temperaturewas refluxed for 24 h
  2. distillationTHF was distilled
  3. customthe residue was purified by column chromatography (silica gel: eluent: hexane/EtOAc 3:1-1:1)

Sources & evidence

ORD record
ord-d412ada58d2c44bcb6d2fd3509df2c39
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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