Benzoyl isothiocyanate → HCID 57503715, compound

HRID 556411Notes

Reaction equation

HRID 556411 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15]([C:17]1[S:32][C:20]2=[N:21][C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:23][C:24]([CH3:25])=[C:19]2[C:18]=1[NH2:33])=[O:16])[CH3:13]>CC(C)=O>[CH2:12]([O:14][C:15]([C:17]1[S:32][C:20]2=[N:21][C:22]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:23][C:24]([CH3:25])=[C:19]2[C:18]=1[NH:33][C:10]([NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[S:11])=[O:16])[CH3:13]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 12201910HCID 12201910, compound

Product 1

HCID 57503715HCID 57503715, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5 ml (13.3 mmol) acetonic benzoyl-isothiocyanate solution (2 M) is added to 2.78 g (8.9 mmol) 3-amino-4-methyl-6-phenyl-thieno[2,3-b]pyridine-2-carboxylic acid ethyl ester in 10 ml acetone and refluxed for 2 h. The precipitate precipitated after cooling is sucked off, washed with some water and ethanol, suck dried and dried in vacuo at 50° C. 3.93 g (93%) 3-(3-benzoylthioureido)-4-methyl-6-phenyl-thieno[2,3-b]pyridine-2-carboxylic acid ethyl ester is obtained.

Workup

  1. temperaturerefluxed for 2 h
  2. customThe precipitate precipitated
  3. temperatureafter cooling
  4. washwashed with some water and ethanol, suck
  5. customdried
  6. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-59f8a130261d48b0b987b817fc68d44f
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Reaction notes

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