Sodium Hydroxide → HCID 57093069, compound

HRID 1108163Notes

Reaction equation

HRID 1108163 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][C:4]([SH:7])=[CH:3][CH:2]=1.Cl[C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:15](=[O:16])([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])[S:7][C:4]1[CH:3]=[CH:2][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 62365Isobutyl chloroformateHCID 27604144-Phenylbenzene-1-thiol2×

Product 1

HCID 57093069HCID 57093069, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 9.3 g of [1,1'-biphenyl]-4-thiol (alternatively named 4'-mercapto-1,1'-biphenyl), 40 mL of dichloromethane, 0.21 g of tetrabutylammonium hydrogen sulfate, and 7.2 g of isobutyl chloroformate was cooled to 5° C. and 10.2 g of 20% aqueous NaOH was added over 10 min. The mixture was allowed to stir for 30 min at 15° C. the phases were separated, and the organic phase was concentrated to dryness. The residue was slurried in 100 mL of cold isopropanol, filtered, and suction-dried to afford 12.9 g (92% yield) of product, m.p. 78-79° C. 1H NMR (CDCl3): δ0.90 (d, 6H), 2.00 (s, 1H), 4.05 (d, 7.35-7.50 (m, 3H), 7.60 (d, 2H), 7.60 (s, 4H).

Workup

  1. customwere separated
  2. concentrationthe organic phase was concentrated to dryness
  3. filtrationfiltered
  4. customsuction-dried

Sources & evidence

ORD record
ord-69ebd77d5c594befa37f1960ef5dfce6
Source dataset
uspto-grants-2000_05
Patent number
US06063932

Reaction notes

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