Sulfuryl chloride → HCID 20295022, compound

HRID 1390130Notes

Reaction equation

HRID 1390130 reaction equation
[C:1]([NH:6][C:7](=[O:12])[CH2:8][C:9]([CH3:11])=[O:10])([O:3][CH2:4][CH3:5])=[O:2].S(Cl)([Cl:16])(=O)=O>C(Cl)Cl>[C:1]([NH:6][C:7](=[O:12])[CH:8]([Cl:16])[C:9]([CH3:11])=[O:10])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 582816Ethyl (3-oxobutanoyl)carbamate

Product 1

HCID 20295022HCID 20295022, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The N-carbethoxyacetoacetamide (12.7 g from above reaction) was dissolved in methylene chloride (50 ml) and cooled in an ice bath. Sulfuryl chloride (10.0 g) was added dropwise to the reaction mixture. After refluxing for 45 minutes the solvent was evaporated under reduced pressure. The resulting colorless oil crystallized over night to give 15.2 g (99%) colorless product. An analytical sample recrystallized from CHCl3 /cyclohexane had mp 69.5°-70.0°; ir (Nujol) 3200, 1760 (broad), 1540 cm-1 ; nmr (CDCl3) 1.35 (t, 3H, J=7), 2.45 (s, 3H), 4.30 (q, 2H, J=7), 5.75 (s, 1H), 9.0 (s, 1H),; and mass spectrum m/e 43 (100%) and 207 (M+).

Workup

  1. temperaturecooled in an ice bath
  2. temperatureAfter refluxing for 45 minutes the solvent
  3. customwas evaporated under reduced pressure
  4. customThe resulting colorless oil crystallized over night

Sources & evidence

ORD record
ord-d21ab71a03d148678b3660edb61565b3
Source dataset
uspto-grants-1981_01
Patent number
US04247712

Reaction notes

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