Chlorosulfonyl isocyanate → HCID 19098295, compound

HRID 1975723Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[C:20]([NH2:22])=[O:21])=[CH:15][CH:14]=1.ClS([N:32]=[C:33]=[O:34])(=O)=O.[C:35](O)(=O)[CH3:36].O>C1COCC1>[C:33]([NH:22][C:20](=[O:21])[CH:19]([C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[CH:18][CH:17]=1)[CH:23]1[CH2:36][CH2:35][CH2:24][CH2:25][CH2:26][CH2:27]1)(=[O:34])[NH2:32]

Participants

Conditions

Temperature: 100 °C

Procedure

10 g (0.0257 mol) of the compound from Example III are suspended in 100 ml of THF at 0° C., and 2.5 ml (4 g/0.028 mol) of chlorosulphonyl isocyanate are added, with exclusion of moisture. The mixture is allowed to after-react for 15 minutes, while stirring, 120 ml of glacial acetic acid/water (2/1) are added and the temperature is allowed to rise to room temperature. To bring the reaction to completion, the mixture is heated at 100° C. for a further 15 minutes, during which a uniform solution forms. The solution is evaporated to dryness in vacuo, and the residue is extracted by stirring with 50 ml of water for 15 minutes and recrystallised from THF/ethylene chloride.

Workup

customto after-react for 15 minutes
customto rise to room temperature
customthe reaction to completion
customThe solution is evaporated to dryness in vacuo
extractionthe residue is extracted
stirringby stirring with 50 ml of water for 15 minutes
customrecrystallised from THF/ethylene chloride

Sources & evidence

ORD record: ord-9f5adf90264b455c8daf86fc2f5c61ac
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05288733

Reaction notes

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