Chlorosulfonyl isocyanate → HCID 15453237, compound

HRID 397305Notes

Reaction equation

HRID 397305 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:5]=2[O:4][C:3]=1[C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27].ClS([N:33]=[C:34]=[O:35])(=O)=O>ClCCl>[Cl:27][C:21]1[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=1[C:19]([C:3]1[O:4][C:5]2[CH:10]=[C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:8]=[CH:7][C:6]=2[C:2]=1[NH:1][C:34]([NH2:33])=[O:35])=[O:28]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 15453235HCID 15453235, compound

Product 1

HCID 15453237HCID 15453237, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

30.9 g (75 mmol) of the compound of example IV or IVa are dissolved in 750 ml dichloromethane and cooled to 0°C. 11.6 g (82 mmol) chlorosulfonyl isocyanate in dichloromethane are added and the mixture is stirred at 0° C. for 30 min and at room temperature for 3 h. The solvent is removed in vacuo, the residue suspended in water and stirred vigorously for 3 h at 60° C. After cooling to r.t. the suspension is filtered, the crude product dried in a desiccator in the presence of phosphorus pentoxide and triturated with diisopropylether at 40° C.;.

Workup

  1. customThe solvent is removed in vacuo
  2. stirringstirred vigorously for 3 h at 60° C
  3. temperatureAfter cooling to r.t. the suspension
  4. filtrationis filtered
  5. dry with materialthe crude product dried in a desiccator in the presence of phosphorus pentoxide
  6. customtriturated with diisopropylether at 40° C.

Sources & evidence

ORD record
ord-1f6c6e3d3f854e1dade351c2f5874caf
Source dataset
uspto-grants-2003_08
Patent number
US06610687B1

Reaction notes

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