Sulfuryl chloride → HCID 86613436, compound

HRID 2357745Notes

Reaction equation

HRID 2357745 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6](=[O:33])(SCC)[O:7][CH2:8][O:9][C:10](=[O:29])[C:11]1[CH:16]=[C:15]([S:17]([NH2:20])(=[O:19])=[O:18])[C:14]([Cl:21])=[CH:13][C:12]=1[NH:22][CH2:23][C:24]1[O:25][CH:26]=[CH:27][CH:28]=1>ClCCl>[C:6]([Cl:4])(=[O:33])[O:7][CH2:8][O:9][C:10](=[O:29])[C:11]1[CH:16]=[C:15]([S:17]([NH2:20])(=[O:19])=[O:18])[C:14]([Cl:21])=[CH:13][C:12]=1[NH:22][CH2:23][C:24]1[O:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 86613435HCID 86613435, compound

Product 1

HCID 86613436HCID 86613436, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Freshly distilled sulfuryl chloride (0.050 mole) in dichloromethane (25 mL) is added to O-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxymethyl) S-ethyl carbonothioate (1005) (0.050 mole) in dichloromethane (25 mL) at 0-5° C. with stirring during 15 minutes followed by stirring at ambient temperature for 45 minutes. The volatiles are removed by evaporation at ambient temperature and then at 20 millibar for 16 hours. The crude product is dissolved in ethyl acetate and applied to a column of silica gel. The column may be eluted with hexanes/ethyl acetate, and the fractions that contain pure product may be combined and spin evaporated in vacuo to give 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxymethyl carbonochloridate (1010). See eg., Folkmann, et al., Synthesis, 1159 (1990), Method G.

Workup

  1. stirringby stirring at ambient temperature for 45 minutes
  2. customThe volatiles are removed by evaporation at ambient temperature
  3. waitat 20 millibar for 16 hours
  4. dissolutionThe crude product is dissolved in ethyl acetate
  5. washThe column may be eluted with hexanes/ethyl acetate
  6. customspin evaporated in vacuo

Sources & evidence

ORD record
ord-011eaebf0b254a7aaf3a72975c13da39
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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