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Hydrochloric Acid → 4-(2-Carbamoyl-2-cyano-thioacetylamino)-benzoic acid t-butyl ester

HRID 33766
Notes
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Reaction equation

HRID 33766 reaction equation
[C:1]([O:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([N:13]=[C:14]=[S:15])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[C:19]([CH2:21][C:22]([NH2:24])=[O:23])#[N:20].Cl>CN(C=O)C>[C:1]([O:5][C:6](=[O:16])[C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14](=[S:15])[CH:21]([C:22](=[O:23])[NH2:24])[C:19]#[N:20])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 14797Potassium HydroxideHCID 4281352tert-Butyl 4-isothiocyanatobenzoate

Product 1

HCID 597976494-(2-Carbamoyl-2-cyano-thioacetylamino)-benzoic acid t-butyl esterYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

4-Isothiocyanato-benzoic acid t-butyl ester 2 (28.3 gm, 120.4 mmol) was taken into DMF (200 ml). To this KOH (6.74 gm, 120.4 mmol) and cyanoacetamide (10.21 gm, 120.4 mmol) were added. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was acidified with 1N HCl, the precipitate obtained was filtered, washed with water, and dried under vacuum, to provide 32.10 gm of 4-(2-Carbamoyl-2-cyano-thioacetylamino)-benzoic acid t-butyl ester 3.

Workup

  1. customthe precipitate obtained
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-25247bd69a724965a3244e1749ab1d8c
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429667B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes