1,2-Diazinane → 2-Chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-thiolbenzoic acid (methoxycarbonylmethyl) ester

HRID 484222Notes

Reaction equation

HRID 484222 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[O:24])[C:8]1[C:13]([C:14]2([Cl:23])[CH2:18][C:17]([F:19])=[C:16]([N:20]=[C:21]=[S:22])[S:15]2)=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][NH:26]1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH2:5][O:6][C:7](=[O:24])[C:8]1[C:13]([C:14]2([Cl:23])[CH2:18][C:17]([F:19])=[C:16]([NH:20][C:21]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][NH:26]3)=[S:22])[S:15]2)=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 1363341,2-DiazinaneHCID 867460252-Chloro-4-fluoro-5-isothiocyanato-thiolbenzoic acid (methoxycarbonylmethyl) ester

Product 1

HCID 867460262-Chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-thiolbenzoic acid (methoxycarbonylmethyl) esterYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4.8 g of 2-chloro-4-fluoro-5-isothiocyanato-thiolbenzoic acid (methoxycarbonylmethyl) ester obtained in accordance with Example P3 in 50 ml of toluene is added dropwise, with stirring, at 20°-25° C. to a solution of 1.4 g of hexahydropyridazine in 20 ml of toluene. Stirring is continued for a further 8 hours at room temperature. Concentration by evaporation in vacuo yields 4.4 g of 2-chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-thiolbenzoic acid (methoxycarbonylmethyl) ester in resinous form.

Workup

  1. additionis added dropwise
  2. concentrationConcentration
  3. customby evaporation in vacuo

Sources & evidence

ORD record
ord-fbe1f65c0eff4c01a6253c5757df2079
Source dataset
uspto-grants-1993_07
Patent number
US05229514

Reaction notes

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