Ethyl chloroformate → HCID 23333519, compound

HRID 904092Notes

Reaction equation

HRID 904092 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([C:9]1[CH:19]=[CH:18][C:12]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].C([O-])([O-])=O.[K+].[K+].Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(#N)C>[CH2:32]([O:31][C:29]([N:13]([S:14]([CH3:17])(=[O:15])=[O:16])[C:12]1[CH:18]=[CH:19][C:9]([C:3]([OH:8])([C:4]([F:7])([F:6])[F:5])[C:2]([F:1])([F:20])[F:21])=[CH:10][CH:11]=1)=[O:30])[CH3:33]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 23333510HCID 23333510, compound

Product 1

HCID 23333519HCID 23333519, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 6.7 g (20 mmole) 4'-(hexafluoro-2-hydroxy-2-propyl)-methanesulfonanilide (prepared as in Example 1) in 100 ml acetonitrile, add 4.1 g (30 mmole) K2CO3 and 2.2 g (20 mmole) ethyl chloroformate. Stir 16 hours, filter and concentrate. Partition the residue between Et2O and 5% Na2CO3. Dry, concentrate and recrystallize first from Et2O-hexane and then from toluene to give the product; m.p. 108°-112° C.

Workup

  1. filtrationfilter
  2. concentrationconcentrate
  3. customPartition the residue between Et2O and 5% Na2CO3
  4. customDry
  5. concentrationconcentrate
  6. customrecrystallize first from Et2O-hexane
  7. customfrom toluene to give the product

Sources & evidence

ORD record
ord-75c75e6b349a43dd8f4b9ef496b2e04d
Source dataset
uspto-grants-1980_10
Patent number
US04230635

Reaction notes

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