Triethylamine → tert-Butyl[(5-chloro-4-isocyanato-2-methoxybenzyl)oxy]dimethylsilane

HRID 630401Notes

Reaction equation

HRID 630401 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:16]([O:17][CH3:18])=[CH:15][C:13]([NH2:14])=[C:12]([Cl:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>ClCCl>[C:4]([Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([Cl:19])[C:13]([N:14]=[C:21]=[O:23])=[CH:15][C:16]=1[O:17][CH3:18])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 671456574-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline2×

Product 1

HCID 86677215tert-Butyl[(5-chloro-4-isocyanato-2-methoxybenzyl)oxy]dimethylsilaneYield 263.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline (intermediate 39; 300 mg, 1 mmol) in 4 ml of dichloromethane was cooled externally with an ice bath while dropping a solution of triphosgene (108 mg; 0.36 mmol) in 5 ml of dichloromethane. Triethylamine (0.28 ml; 2.01 mmol) was added slowly and the system stirred at room temperature for 3 hr. Half of the solvent is then evaporated in vacuo and 25 ml of pentane added. The white precipitate of ureas was filtered and the filtrate evaporated to dryness giving 311 mg of the title compound that were used without further purification in the next step.

Workup

  1. customHalf of the solvent is then evaporated in vacuo and 25 ml of pentane
  2. additionadded
  3. filtrationThe white precipitate of ureas was filtered
  4. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-b0c458e68b334e239569b44e92965211
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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