Thiophosgene → HCID 178497334, compound

HRID 409994Notes

Reaction equation

HRID 409994 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].[C:13](Cl)(Cl)=[S:14]>C1COCC1>[SH:14][C:13]1[O:12][C:3]2[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Product 1

HCID 178497334HCID 178497334, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-amino-3-hydroxybenzoate (4.45 g, 26.6 mmol) in THF (250 ml) at room temperature, thiophosgene (2.4 mL, 32 mmol) was added slowly via a syringe pump over a period of 1 hr. After stirring for 4 hr, excess thiophosgene was quenched by addition of a saturated aqueous solution of NH4Cl (100 mL), and the THF was removed by evaporation under reduced pressure. More water was added, and the aqueous mixture was extracted with EtOAc (3×). The Combined organic phase was washed with brine, dried (MgSO4), concentrated in vacuo to give Compound 4 as a tan solid. LC-MS, M+1=210

Workup

  1. customexcess thiophosgene was quenched by addition of a saturated aqueous solution of NH4Cl (100 mL)
  2. customthe THF was removed by evaporation under reduced pressure
  3. additionMore water was added
  4. extractionthe aqueous mixture was extracted with EtOAc (3×)
  5. washThe Combined organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2385318b08c549e7a895bab9046672cf
Source dataset
uspto-grants-2014_06
Patent number
US08759539B2

Reaction notes

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