Hydrogen Sulfide → Carbamic acid, (2-amino-1,1-dimethyl-2-thioxoethyl)-, 1,1-dimethylethyl ester

HRID 483974Notes

Reaction equation

HRID 483974 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:13])([CH3:12])[C:10]#[N:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[SH2:14].C(N(CC)CC)C>C1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:13])([CH3:12])[C:10](=[S:14])[NH2:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 18316698tert-butyl N-(1-cyano-1-methylethyl)carbamate

Product 1

HCID 15186362Carbamic acid, (2-amino-1,1-dimethyl-2-thioxoethyl)-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-tert-Butyloxycarbonylamino-2-methylpropiononitrile (80.00 g) in Benzene (700 ml) was stirred at 0° C., and saturated with hydrogen sulfide. To the reaction mixture was dropped triethyl amine (1000 ml) and bubbled hydrogen sulfide at ambient temperature for 9 hours, and left at the same temperature for 19 hours. The reaction mixture was added to water and extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogencarbonate, water and brine, and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo. The residue was washed with n-hexane, to give 2-tert-butyloxycarbonylamino-2-methylpropanethioamide (80.14 g).

Workup

  1. custombubbled hydrogen sulfide at ambient temperature for 9 hours
  2. additionThe reaction mixture was added to water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, saturated aqueous sodium hydrogencarbonate, water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. customthe filtrate was evaporated in vacuo
  8. washThe residue was washed with n-hexane

Sources & evidence

ORD record
ord-99b4fb610a9441929d04646b6c539d98
Source dataset
uspto-grants-1993_07
Patent number
US05229386

Reaction notes

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