Ammonia → tert-butyl N-(carbamothioylmethyl)carbamate

HRID 1376588Notes

Reaction equation

HRID 1376588 reaction equation
N.[SH2:2].[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]#[N:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].O>CO>[C:3]([O:7][C:8]([NH:10][CH2:11][C:12](=[S:2])[NH2:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 402Hydrogen SulfideHCID 962WaterHCID 545844tert-butyl N-(cyanomethyl)carbamate

Product 1

HCID 5324304tert-butyl N-(carbamothioylmethyl)carbamateYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

25 g of ammonia gas and 50 g of hydrogen sulfide gas were successively dissolved in 230 ml of methanol with ice-cooling and stirring. To this was added 71.45 g of (tert-butoxycarbonylamino)acetonitrile, and the mixture was stirred overnight at room temperature. The reaction solution was cooled with ice. To this was slowly added 500 ml of water, and the mixture was stirred for an additional 2 hours with ice- cooling. The crystals precipitated were collected by filtration, washed with 300 ml of cold water, and then dried under reduced pressure to give 65.88 g of (tert-butoxycarbonyl-amino)acetothioamide as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight at room temperature
  3. temperatureThe reaction solution was cooled with ice
  4. stirringthe mixture was stirred for an additional 2 hours with ice-
  5. temperaturecooling
  6. customThe crystals precipitated
  7. filtrationwere collected by filtration
  8. washwashed with 300 ml of cold water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-e47cef37de804429998bc60c0e9f48d5
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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