Chlorosulfonyl isocyanate → HCID 22481941, compound

HRID 2181615Notes

Reaction equation

HRID 2181615 reaction equation
[CH2:1]([O:8][CH:9]([CH3:13])[C:10]([NH2:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClS([N:18]=[C:19]=[O:20])(=O)=O>C(#N)C>[CH2:1]([O:8][CH:9]([CH3:13])[C:10]([NH:12][C:19]([NH2:18])=[O:20])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 34496066183-20-8

Product 1

HCID 22481941HCID 22481941, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 2-benzyloxy-propionamide (Helv. Chim. Acta, 1971, 845-851) (26.6 mmol, 4.77 g) in acetonitrile (100 mL) at room temperature was added dropwise chlorosulfonyl isocyanate (26.6 mmol, 4.1 mL) in acetonitrile (20 mL). After 1 h the reaction was concentrated, then carefully quenched with water (20 mL) and allowed to stir at room temperature for 1 h. The precipitated solid was filtered, collected and air-dried to obtain (2-benzyloxy-propionyl)-urea (62%, 3.66 g); NMR 1.2 (d, 3H), 4.0 (t, 1H), 4.4 (dd, 2H), 7.3 (m, 5H), 7.7 (s, 1H), 10.0 (S, 1H). The above reaction conditions were followed to convert (2-benzyloxy-propionyl)-urea to 2-benzyloxy-N-ureidocarbonyl-propionamide, using the above compound, (2-benzyloxy-propionyl)-urea (16.5 mmol, 3.66 g), chlorosulfonyl isocyanate (28.8 mmol, 2.5 mL), and acetonitrile (80 mL). The yield of 2-benzyloxy-N-ureidocarbonyl-propionamide was 59% (2.56 g); NMR 1.4 (d, 3H), 4.2 (t, 1H), 4.6 (dd, 2H), 7.4 (m, 5H), 9.8 (s, 1H), 11.1 (s, 1H).

Workup

  1. concentrationAfter 1 h the reaction was concentrated
  2. customcarefully quenched with water (20 mL)
  3. filtrationThe precipitated solid was filtered
  4. customcollected
  5. customair-dried

Sources & evidence

ORD record
ord-83074d561bc441fb88f894cc23d03bd8
Source dataset
uspto-grants-2005_05
Patent number
US06894047B2

Reaction notes

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