Thiophosgene → HCID 118436176, compound

HRID 1775488Notes

Reaction equation

HRID 1775488 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:17]=[CH:16][C:7]([C:8]([O:10][CH2:11][C:12]([NH2:15])([CH3:14])[CH3:13])=[O:9])=[CH:6][CH:5]=1.C([O-])([O-])=O.[Na+].[Na+].[C:24](Cl)(Cl)=[S:25]>C(Cl)Cl>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:11][C:12]([N:15]=[C:24]=[S:25])([CH3:14])[CH3:13])=[O:9])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 118436420HCID 118436420, compound

Product 1

HCID 118436176HCID 118436176, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A biphasic mixture of 2-amino-2-methylpropyl 4-methoxybenzoate hydrochloride (0.24 g, 0.92 mmol), DCM (9.2 mL) and saturated aqueous Na2CO3 (18.5 mL) was cooled to 0° C. Thiophosgene (0.35 mL, 4.62 mmol) was added and the mixture was stirred for 15 min. The organic layer was separated, dried with Na2SO4, filtered and concentrated to give the title compound (0.24 g, 99%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.17-7.92 (m, 2 H), 7.06-6.81 (m, 2 H), 4.27 (s, 2 H), 3.89 (s, 3 H), 1.50 (s, 6 H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1b3bde8a6a38446dbf38774c5fff53b2
Source dataset
uspto-grants-2016_02
Patent number
US09260439B2

Reaction notes

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