Thionyl Chloride → 9h-Fluoren-9-ylmethyl[5-(chlorosulfonyl)-2,4-dimethylphenyl]carbamate

HRID 1802461Notes

Reaction equation

HRID 1802461 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3[C:20]([CH3:30])=[CH:21][C:22]([CH3:29])=[C:23]([S:25](O)(=[O:27])=[O:26])[CH:24]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:33])=O>CN(C=O)C>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:17])[NH:18][C:19]3[CH:24]=[C:23]([S:25]([Cl:33])(=[O:27])=[O:26])[C:22]([CH3:29])=[CH:21][C:20]=3[CH3:30])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 594360375-{[(9h-Fluoren-9-ylmethoxy)carbonyl]amino}-2,4-dimethylbenzenesulfonic acid

Product 1

HCID 594360429h-Fluoren-9-ylmethyl[5-(chlorosulfonyl)-2,4-dimethylphenyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2,4-dimethylbenzenesulfonic acid (5 g, 11.8 mmol) in DMF (5.9 mL) was added thionyl chloride (4.3 mL, 59.0 mmol). The reaction was stirred at room temperature for three hours and then quenched by the addition of water. The colorless precipitate was then collected by filtration and dried in vacuo to afford 9H-fluoren-9-ylmethyl[5-(chlorosulfonyl)-2,4-dimethylphenyl]carbamate as a colorless solid.

Workup

  1. customquenched by the addition of water
  2. filtrationThe colorless precipitate was then collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-14653f18d27f4d50bddc9fbd21bff40d
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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