Dichloromethane → 1-(Tert-butyldiphenylsilyloxymethyl)-2,6-dichloro-3-(phthalimidoacetylamino)benzene

HRID 636475Notes

Reaction equation

HRID 636475 reaction equation
[NH2:1][C:2]1[C:3]([Cl:28])=[C:4]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([Cl:8])=[CH:6][CH:7]=1.ClCCl.[C:32]1(=[O:46])[N:36]([CH2:37][C:38](Cl)=[O:39])[C:35](=[O:41])[C:34]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:33]12>O>[Si:11]([O:10][CH2:9][C:4]1[C:5]([Cl:8])=[CH:6][CH:7]=[C:2]([NH:1][C:38](=[O:39])[CH2:37][N:36]2[C:35](=[O:41])[C:34]3=[CH:42][CH:43]=[CH:44][CH:45]=[C:33]3[C:32]2=[O:46])[C:3]=1[Cl:28])([C:24]([CH3:25])([CH3:27])[CH3:26])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 105987193-(Tert-butyldiphenylsilyloxymethyl)-2,4-dichloroaniline

Product 1

HCID 108415181-(Tert-butyldiphenylsilyloxymethyl)-2,6-dichloro-3-(phthalimidoacetylamino)benzeneYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-amino-1-(tert-butyldiphenylsilyloxy-methyl)-2,6-dichlorobenzene (348 mg) triethylamine (0.15 ml) and dichloromethane (3.5 ml) was added phthalimidoacetyl chloride (186 mg) under ice-cooling, and the mixture was stirred for 1.5 hours at ambient temperature. Water was added thereto, and the resulting precipitates were collected by vacuum filtration and washed with diisopropyl ether to give 1-(tert-butyldiphenylsilyloxymethyl)-2,6-dichloro-3-(phthalimidoacetylamino)benzene (460 mg) as crystals.

Workup

  1. temperaturecooling
  2. customthe resulting precipitates
  3. filtrationwere collected by vacuum filtration
  4. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-bdee257fae4b4e9485a988d9f25fb7ec
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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