tert-Butyl isothiocyanate → HCID 53716090, compound

HRID 372586Notes

Reaction equation

HRID 372586 reaction equation
[C:1]([NH:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[OH-].[Na+].[C:18]([N:22]=[C:23]=[S:24])([CH3:21])([CH3:20])[CH3:19]>O.C(O)C>[C:1]([NH:4][CH:5]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:23]([NH:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[S:24])=[CH:13][CH:14]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11544tert-Butyl isothiocyanateHCID 14798Sodium HydroxideHCID 14037275HCID 14037275, compound

Product 1

HCID 53716090HCID 53716090, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of α-acetamido-p-aminophenylacetic acid (1.04 g, 5 mmol) in water (5 ml) was added 10% NaOH until solution was effected. The solution was diluted with an equal volume of ethanol and then t-butyl isothiocyanate (1.64 g, 15 mmol) in ethanol was added. The reaction was stirred at room temperature overnight and then refluxed 24 hours. The ethanol was evaporated in vacuo and the aqueous phase was acidified and filtered. The aqueous filtrate was extracted with ethyl acetate. The dried extracts were evaporated to give α-acetamido-p-(3-t-butylthioureido)phenylacetic acid.

Workup

  1. temperaturerefluxed 24 hours
  2. customThe ethanol was evaporated in vacuo
  3. filtrationfiltered
  4. extractionThe aqueous filtrate was extracted with ethyl acetate
  5. customThe dried extracts were evaporated

Sources & evidence

ORD record
ord-8ce5e191eb404c668782ab77d462b820
Source dataset
uspto-grants-1978_05
Patent number
US04091227

Reaction notes

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