4-Chlorophenyl Isocyanate → HCID 58882012, compound

HRID 552127Notes

Reaction equation

HRID 552127 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([OH:12])[C:9]([OH:11])=[O:10].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1>ClCCl.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([O:12][C:21](=[O:22])[NH:20][C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 2733641(-)-2-Chloromandelic acid

Product 1

HCID 58882012HCID 58882012, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 6344DichloromethaneSolvent

Procedure

1 g (5 mmol) of (R)-(2-chlorophenyl)hydroxyacetic acid are dissolved in 10 ml of dichloromethane, and 0.77 g (5 mmol) of 4-chlorophenyl isocyanate and 50 mg of dibutyltin dilaurate are added successively, and the mixture is stirred for 16 hours. Conventional work-up gives 1.5 g of (R)-(2-chlorophenyl)(4-chlorophenylcarbamoyloxy)acetic acid.

Sources & evidence

ORD record
ord-a0b2b635fca0497a8047174171d70d40
Source dataset
uspto-grants-2011_05
Patent number
US07951804B2

Reaction notes

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