Methanol → HCID 178501461, compound

HRID 903385Notes

Reaction equation

HRID 903385 reaction equation
[N:1]#[N:2].[S:3]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:27])[NH2:26])([C:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:11]([N:12]([CH3:14])[CH3:13])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4].S(Cl)([Cl:33])=O.[CH3:35]O>>[N:1]#[N:2].[OH2:4].[ClH:33].[ClH:33].[CH3:35][O:29][C:28](=[O:30])[C@H:20]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:26])[NH2:27])[NH:19][S:3]([C:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:11]([N:12]([CH3:13])[CH3:14])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178482655HCID 178482655, compound

Product 1

HCID 178501461HCID 178501461, compoundYield 92%

Procedure

To an ice-cooled suspension of 1.0 gram of N2 -dansyl-L-arginine in 15 ml of methanol was added dropwise 0.5 ml of thionyl chloride with vigorous stirring. After being allowed to stand for 2 hours at room temperature, the reaction mixture was refluxed for 2 hours, and was evaporated to dryness (syrup). Treatment of the residual syrup with cold ethyl ether and a small amount of water gave crude crystals. After recrystallization from methanol-ethyl ether, colorless N2 -dansyl-L-arginine methyl ester dihydrochloride monohydrate was obtained in 92% yield; mp. 147°-150° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. customwas evaporated to dryness (syrup)
  3. customTreatment of the residual syrup with cold ethyl ether and a small amount of water gave crude crystals
  4. customAfter recrystallization from methanol-ethyl ether

Sources & evidence

ORD record
ord-dbdfd2d8a2704f51b235b7c1d4b77398
Source dataset
uspto-grants-1980_10
Patent number
US04227006

Reaction notes

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