Chlorotrimethylsilane → 3-(Methylsulphonyl)-2-oxoimidazolidine-1-carbonyl chloride

HRID 1283012Notes

Reaction equation

HRID 1283012 reaction equation
[CH3:1][S:2]([N:5]1[CH2:9][CH2:8][NH:7][C:6]1=[O:10])(=[O:4])=[O:3].C[Si](C)(C)[Cl:13].C(N(CC)CC)C.[O:23]1[CH2:28]COCC1>>[Cl:13][C:28]([N:7]1[CH2:8][CH2:9][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]1=[O:10])=[O:23]

Participants

5

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 30162961-(Methylsulphonyl)imidazolidin-2-one

Product 1

HCID 30162993-(Methylsulphonyl)-2-oxoimidazolidine-1-carbonyl chloride

Procedure

16.4 parts by weight of 1-methylsulphonyl-imidazolid- 2-one in dioxane were boiled for 3 days with 27 parts by weight of trimethylchlorosilane and 20 parts by weight of triethylamine. The triethylamine hydrochloride which precipitated was filtered off, 11 parts by weight of phosgene were added to the filtrate and the mixture was left to stand overnight at room temperature. It was then evaporated to dryness and the residue recrystallized from boiling acetone.

Workup

  1. customThe triethylamine hydrochloride which precipitated
  2. filtrationwas filtered off
  3. addition11 parts by weight of phosgene were added to the filtrate
  4. waitthe mixture was left
  5. customIt was then evaporated to dryness
  6. customthe residue recrystallized

Sources & evidence

ORD record
ord-d56c3a5421054171a2ace8d07363aa50
Source dataset
uspto-grants-1976_08
Patent number
US03974141

Reaction notes

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