Thionyl Chloride → HCID 15346296, compound

HRID 1081954Notes

Reaction equation

S(Cl)([Cl:3])=O.[ClH:5].O[CH2:7][C:8]1[CH:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][C:9]=1[N:10]([CH3:12])[CH3:11]>>[ClH:3].[Cl:5][CH2:7][C:8]1[CH:16]=[CH:15][C:14]([CH2:17][Cl:3])=[CH:13][C:9]=1[N:10]([CH3:12])[CH3:11]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 19975051HCID 19975051, compound3×

Product 1

HCID 15346296HCID 15346296, compoundYield 77%

Procedure

Thionyl chloride (35 ml) was added to 2 grams (0.00919 mol) of 2,5-bis(hydroxymethyl)-N,N-dimethylaniline hydrochloride, VIII. The 2,5-bis(hydroxymethyl)-N,N-dimethylaniline hydrochloride (VIII) went into solution immediately, accompanied by evolution of heat and gas. The reaction was stirred for several minutes. The volatiles were removed under reduced pressure to yield 2.38 g of crystalline residue, compound IX. The solid IX was dissolved in a minimum amount of hot acetonitrile; the solution was filtered, and an equivalent amount of ethyl acetate added and the solution cooled. Yield 77%. Elemental analysis: calcd for C10H14Cl3N: C, 47.18; H, 5.54: Cl, 41.78,; N, 5.50. Found: C,47.04; H, 5.54; N, 5.34

Workup

temperatureof heat
customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-9c0c60a15acd440db77523c4888bd925
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05587488

Reaction notes

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