Methyl Isocyanate → (R,S)-Bis-(1-methyl-2,5-dioxo-4-imidazolidinyl-methyl)-disulphide

HRID 1073235

Reaction equation

HRID 1073235 reaction equation
[CH2:1]([S:7][S:8][CH2:9][C@H:10]([NH2:14])[C:11]([OH:13])=O)[C@H:2]([NH2:6])[C:3]([OH:5])=O.[CH3:15][N:16]=[C:17]=[O:18]>[OH-].[Na+]>[CH3:15][N:16]1[C:11](=[O:13])[C@H:10]([CH2:9][S:8][S:7][CH2:1][C@@H:2]2[C:3](=[O:5])[N:16]([CH3:15])[C:17](=[O:18])[NH:6]2)[NH:14][C:17]1=[O:18]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 67678(-)-Cystine

Product 1

HCID 88616268(R,S)-Bis-(1-methyl-2,5-dioxo-4-imidazolidinyl-methyl)-disulphide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of L-cystine (12 g) and 2 molar sodium hydroxide solution (50 ml), cooled to 0°-5° C. in an ice bath, was added, dropwise, methyl isocyanate (8.55 g). The clear solution was stirred at 0° for 2 hours, and then at room temperature over night.

Workup

  1. temperaturecooled to 0°-5° C. in an ice bath
  2. additionwas added
  3. waitat room temperature over night

Sources & evidence

ORD record
ord-a01e2a8168c54280999c179befc67799
Source dataset
uspto-grants-1990_11
Patent number
US04968711

Linked notes

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