N,N-Dimethylaniline → HCID 88627047, compound

HRID 1194897Notes

Reaction equation

Br[CH2:2][C:3](=O)/[C:4](=[N:10]/[O:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[CH3:18])/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:20][C:21]([NH2:23])=[S:22].CN(C)C1C=CC=CC=1>>[NH2:23][C:21]1[S:22][CH:2]=[C:3](/[C:4](=[N:10]/[O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[CH3:18])/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:20]=1

Participants

Reactant 3

HCID 949N,N-Dimethylaniline

HCID 2723790Thiourea

HCID 88626973HCID 88626973, compound

Product 1

HCID 88627047HCID 88627047, compoundYield 45.9%

Procedure

Ethyl 4-bromo-(Z)-2-(trans-2-methylcyclohexyl-oxyimino)-3-oxobutyrate (2.5 g) was treated with thiourea (0.57 g) and N,N-dimethylaniline (0.95 ml) as described in Example 4d to give the title compound as a yellow gum (1.07 g) after silica gel chromatography. (Found: M+, 311.1297. C14H21N3O3S requires M, 311.1305); νmax (CH2Cl2) 3475, 3380, 1735, 1600 and 1525 cm-1 ; δH (CDCl3) 0.98 (3H, d, J 6 Hz), 1.35 (3H, t, J 7 Hz), ca 1.1-2.4 (9H, m), 3.84 (1H, m), 4.40 (2H, q, J 7 Hz), 5.88 (2H, broad s), 6.71 (1H, s).

Sources & evidence

ORD record: ord-e9407feb6b9741a9a4715f470f2944c8
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04816452

Reaction notes

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