Thiourea → HCID 88627279, compound

HRID 1194890Notes

Reaction equation

HRID 1194890 reaction equation
Br[CH2:2][C:3](=O)/[C:4](=[N:10]/[O:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:19][C:20]([NH2:22])=[S:21]>>[NH2:22][C:20]1[S:21][CH:2]=[C:3](/[C:4](=[N:10]/[O:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:19]=1

Participants

3

Reactant 2

HCID 2723790ThioureaHCID 88627518HCID 88627518, compound

Product 1

HCID 88627279HCID 88627279, compoundYield 70%

Procedure

Ethyl 4-bromo-(Z)-2-(tetrahydro-4H-pyran-4-yloxyimino)-3-oxobutyrate (0.52 g) was treated with thiourea as described in Example 4d. Crystallisation from diisopropyl ether gave the title compound as a pale yellow solid (0.34 g, 70%), m.p. 110.0°-110.5° C. [Found: C: 48.37, H: 5.99, N: 13.59. C12H17N3O4S requires C: 48.15, H: 5.72, N: 14.04%]. νmax (KBr) 3138, 1733, 1616, 1538 cm-1. δH (CDCl3) 1.39 (3H, t), 1.76 (2H, m), 2.01 (2H, m), 3.56 (2H, m), 3.88 (2H, m), 4.42 (2H, q), 4.53 (1H, m), 5.29 (2H, br s, exch. D2O), 6.73 (1H, s).

Workup

  1. customCrystallisation from diisopropyl ether

Sources & evidence

ORD record
ord-9db32891e23e450fb8a322a0bd862558
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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