N,N-Dimethylaniline → HCID 21248888, compound

HRID 1194921Notes

Reaction equation

HRID 1194921 reaction equation
Br[CH2:2][C:3](=O)/[C:4](=[N:10]/[O:11][CH2:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20])/[C:5]([O:7][CH2:8][CH3:9])=[O:6].CN(C)C1C=CC=CC=1.[NH2:31][C:32]([NH2:34])=[S:33]>C(O)C>[NH2:34][C:32]1[S:33][CH:2]=[C:3](/[C:4](=[N:10]/[O:11][CH2:12][C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:31]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 2723790ThioureaHCID 21249071HCID 21249071, compound

Product 1

HCID 21248888HCID 21248888, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-bromo-(Z)-2-(2,6-dichlorobenzyloxyimino)-3-oxobutyrate (7.2 g) was dissolved in ethanol (20 ml) and N,N-dimethylaniline (2.33 ml) and thiourea (1.4 g) added with stirring. After 18 h the title compound was filtered off, washed with ethanol and dried (4.9 g), m.p. 171°-2° C., νmax (KBr) 3423, 1722, 1619, 1529, 1284, 1188, 1021, and 995 cm-1, δH [(CD3)2SO]1.22 (3H, t), 4.33 (2H, q), 5.51 (2H, s), 6.96 (1H, s), 7.24 (2H, br s), and 7.54 (3H, m), [Mass spectrum: M+ (373/375)].

Workup

  1. filtrationAfter 18 h the title compound was filtered off
  2. washwashed with ethanol
  3. dry with materialdried (4.9 g), m.p. 171°-2° C., νmax (KBr) 3423, 1722, 1619, 1529, 1284, 1188, 1021, and 995 cm-1, δH [(CD3)2SO]1.22 (3H, t), 4.33 (2H, q), 5.51 (2H, s), 6.96 (1H, s), 7.24 (2H, br s), and 7.54 (3H, m), [Mass spectrum: M+ (373/375)]

Sources & evidence

ORD record
ord-19439fad1d5d4231baf2f43035e569e1
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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