Thionyl Chloride → HCID 70217041, compound

HRID 2270891Notes

Reaction equation

HRID 2270891 reaction equation
S(Cl)(Cl)=O.ClCC1C=C(NC(C2C=CC=CC=2)C(OC)=O)C=CC=1.[N-]=[N+]=[N-].[Na+].[N:29]([CH2:32][C:33]1[CH:34]=[C:35]([NH:39][CH:40]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:41]([O:43][CH3:44])=[O:42])[CH:36]=[CH:37][CH:38]=1)=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[NH2:29][CH2:32][C:33]1[CH:34]=[C:35]([NH:39][CH:40]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:41]([O:43][CH3:44])=[O:42])[CH:36]=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 70215480HCID 70215480, compoundHCID 86757685HCID 86757685, compound

Product 1

HCID 70217041HCID 70217041, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Equimolar amounts of methyl (R,S)-2-bromo-2-phenylacetate and 3-hydroxymethylaniline are reacted to give methyl N-(3-hydroxymethylphenyl)aminophenyl-acetate. By reaction with thionyl chloride to give methyl N-(3-chloromethylphenyl)aminophenylacetate and subsequent reaction with sodium azide, methyl N-(3-azidomethylphenyl)aminophenylacetate (“A”) is obtained. A solution of 9.2 g of “A” in 350 ml of ethyl acetate is hydrogenated for 35 minutes in the presence of 1 g of Pd/C (5%). After removing the catalyst and the solvent, methyl N-(3-aminomethylphenyl)aminophenyl-acetate) (“B”) is obtained as an oil, RT 19.5; FAB 271.

Workup

  1. customto give
  2. customis obtained
  3. customAfter removing the catalyst

Sources & evidence

ORD record
ord-ef17674d81224496b30e055192964881
Source dataset
uspto-grants-2001_12
Patent number
US06333308B1

Reaction notes

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