Benzoyl isothiocyanate → 4-Thiocarbamoyl-1,4-diazepane-1-carboxylic acid tert-butyl ester

HRID 1401843Notes

Reaction equation

HRID 1401843 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:23]=[C:24]=[S:25])(=O)C1C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:24](=[S:25])[NH2:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 866718274-Thiocarbamoyl-1,4-diazepane-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1.37 g (6.85 mmol) of 1,4-diazepane-1-carboxylic acid tert-butyl ester and 1.12 g (6.85 mmol) of benzoyl isothiocyanate were dissolved in 13 ml of THF and stirred at 50° C. for 2 h. The solvent was subsequently distilled off, and the residue was taken up in 34 ml of methanol and 3.4 ml of water, and 1.89 g of potassium carbonate were added. The mixture was boiled under reflux overnight and then filtered off. The filtrate was evaporated, slurried in 80 ml of water and extracted 3 times with 20 ml of EA each time. The organic phase was dried over sodium sulfate, filtered, evaporated, digested using a little PE and EA and filtered off with suction.

Workup

  1. distillationThe solvent was subsequently distilled off
  2. addition3.4 ml of water, and 1.89 g of potassium carbonate were added
  3. temperatureunder reflux overnight
  4. filtrationfiltered off
  5. customThe filtrate was evaporated
  6. extractionextracted 3 times with 20 ml of EA each time
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-2766fc20ae684a639b578d40b9bd6f7d
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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