Chlorosulfonyl isocyanate → HCID 140355106, compound

HRID 982354Notes

Reaction equation

HRID 982354 reaction equation
[CH2:1]([NH:8][CH:9]([CH2:12]Cl)[C:10]#[N:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClS([N:18]=C=O)(=O)=O.[C:21](=[O:24])([O-])O.[Na+]>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([N:8]1[C:9](=[CH2:12])[C:10](=[NH:18])[NH:11][C:21]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 20067654HCID 20067654, compound

Product 1

HCID 140355106HCID 140355106, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of 4 g. (17.3 mmol) 2-benzylamino-3-chloropropionitrile in 40 ml. dry methylene chloride and 2.4 ml. triethylamine is added dropwise a solution of 1.64 ml. (18.9 mmol) chlorosulphonyl isocyanate in 20 ml. dry methylene chloride. Subsequently, the reaction solution is further stirred for 2 hours at 0° C., then warmed to ambient temperature and mixed with 300 ml. of a 5% aqueous solution of sodium hydrogen carbonate. The organic phase is then separated off, dried over anhydrous sodium sulphate and evaporated to dryness. Subsequently, the residue is chromatographed on silica gel (elution age t: merhaol/methylene chloride 1:10 v/v) to give 0.8 g. (24% of theory) of the title compound; m.p. 225° C.

Workup

  1. temperaturewarmed to ambient temperature
  2. additionmixed with 300 ml
  3. customThe organic phase is then separated off
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to dryness
  6. customSubsequently, the residue is chromatographed on silica gel (elution age t: merhaol/methylene chloride 1:10 v/v)
  7. customto give 0.8 g

Sources & evidence

ORD record
ord-40ae545434bd47d0a11b19fd3995597c
Source dataset
uspto-grants-1991_02
Patent number
US04996219

Reaction notes

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