Benzyl mercaptan → HCID 54681312, compound

HRID 613110Notes

Reaction equation

HRID 613110 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:14])[CH:3]=1.[CH2:15]([SH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[K+].[Br-]>C(O)(=O)C>[CH:26]1([CH2:27][CH:28]([C:3]2[C:4](=[O:14])[O:5][C:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:7][C:2]=2[OH:1])[S:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 7509Benzyl mercaptanHCID 8082PiperidineHCID 253877Potassium BromideHCID 546956304-Hydroxy-6-phenyl-2H-pyran-2-one

Product 1

HCID 54681312HCID 54681312, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared by Method C using 4-hydroxy-6-phenyl-2H -pyran-2-one (1.5 g, 7.98 mmol), 2-cyclopropylmethylcarboxaldehyde (0.67 g, 7.98 mmol), benzylmercaptan (1.98 g, 15.96 mmol), piperidine, (0.5 mL), acetic acid (0.5 mL). m.p. 59-61° C.; 1H NMR (400 MHz, DMSO-d6) δ-0.97 (m, 2 H), 0.28 (m, 2 H), 0.58 (m, 1 H), 1.61 (m, 1 H), 2.01 (m, 1 H), 3.72 (ABXq, 2 H), 4.22 (q, 1H), 6.67 (s, 1H), 7.18 (t, 1H), 7.25 (d, 2H), 7.31 (t, 2H), 7.53 (m, 3H), 7.75 (m, 2H); IR (KBr) 3061, 2919, 2631, 1649, 1564, 1404, 1267, 766, 691 cm-1 ; MS (CI) m/e 255 ((M-SBzl), 19), 201 (5), 147 (2); Analysis calc'd for C23H2203S1: C, 72.99; H, 5.86; found: C, 72.31; H, 6.08.

Sources & evidence

ORD record
ord-4452d54a8c1d49f587908105d5527fc5
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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