Ethyl 2-chloroethanecarboximidate hydrochloride → HCID 69687596, compound

HRID 1265604Notes

Reaction equation

HRID 1265604 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[CH3:8][O:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([NH:19][NH2:20])=[S:18])[CH:12]=1.Cl.C(OC(=N)CCl)C>CCO.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[S:18][C:2]([CH2:3][OH:4])=[N:20][N:19]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 86586796HCID 86586796, compound

Product 1

HCID 69687596HCID 69687596, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-hydrazinothiocarbonyl-benzoic acid methyl ester trifluoroacetate (0.49 g) and 2-chloro-acetimidic acid ethyl ester hydrochloride (0.47 g) in EtOH (6 mL) was heated to 80° C. for 2.5 h. The mixture was diluted with AcOEt and washed with 1N HCl and with brine. The organic layer was dried and evaporated. The residual oil (0.8 g) was dissolved in MeOH (5 mL), MeONa (0.08 g) was added and the solution was heated to 65° C. for 0.5 h. The mixture was diluted with AcOEt and washed with 1N HCl and with brine. The organic layer was dried and evaporated and the residue was crystallized from AcOEt/hexane to give 3-(5-hydroxymethyl-[1,3,4]thiadiazol-2-yl) -benzoic acid methyl ester (0.15 g) as a white solid, MS (ISP) 251.2 [(M+H)+].

Workup

  1. washwashed with 1N HCl and with brine
  2. customThe organic layer was dried
  3. customevaporated
  4. dissolutionThe residual oil (0.8 g) was dissolved in MeOH (5 mL)
  5. additionMeONa (0.08 g) was added
  6. temperaturethe solution was heated to 65° C. for 0.5 h
  7. additionThe mixture was diluted with AcOEt
  8. washwashed with 1N HCl and with brine
  9. customThe organic layer was dried
  10. customevaporated
  11. customthe residue was crystallized from AcOEt/hexane

Sources & evidence

ORD record
ord-cb61eb6840f34fd2ad7c129baaf527e0
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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