Dimethylformamide diethylacetal → 3-(Dimethylamino)-2-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]acrylic acid methyl ester

HRID 242231Notes

Reaction equation

HRID 242231 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[S:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=1)C.C(O[CH:19](OCC)[N:20]([CH3:22])[CH3:21])C>>[CH3:1][O:3][C:4](=[O:15])[C:5]([C:6]1[S:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=1)=[CH:19][N:20]([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 687550795-(Trifluoromethyl)-1,3,4-thiadiazol-2-ylacetic acid ethyl ester

Product 1

HCID 674565093-(Dimethylamino)-2-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]acrylic acid methyl ester

Procedure

3.05 g (13.5 mmol) 5-(trifluoromethyl)-1,3,4-thiadiazol-2-ylacetic acid ethyl ester [for preparation see DE 42 40 168-A1] are heated in 6.9 ml (40.5 mmol) dimethylformamide diethyl acetal overnight at 100° C. After cooling, the mixture is concentrated and the residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. customthe residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-07dd5932190f4f0087ae7f4892ccfbf9
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Reaction notes

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