(Iodomethyl)cyclohexane → 5-(4-Cyclohexylmethyl-2-hydroxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660778Notes

Reaction equation

HRID 660778 reaction equation
C([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19](CC[Si](C)(C)C)[C:18](=[O:29])[CH2:17]1)C1C=CC=CC=1.I[CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH:32]1([CH2:31][C:13]2[CH:12]=[CH:11][C:10]([N:16]3[S:20](=[O:21])(=[O:22])[NH:19][C:18](=[O:29])[CH2:17]3)=[C:9]([OH:8])[CH:14]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 230414(Iodomethyl)cyclohexaneHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 577774055-(4-Cyclohexylmethyl-2-hydroxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Procedure

The title compound is prepared from 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one and iodomethylcyclohexane analogous to Example 57, steps B, C and D: (M−1)−=323. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.89 (d, J=11.37 Hz, 2 H) 1.09-1.19 (m, 2 H) 1.14 (d, J=9.60 Hz, 1 H) 1.44 (dd, J=14.78, 3.66 Hz, 1 H) 1.62 (d, J=10.86 Hz, 5 H) 2.34 (d, J=7.07 Hz, 2 H) 4.00 (s, 2 H) 6.54 (dd, J=7.96, 1.89 Hz, 1 H) 6.61 (d, J=1.77 Hz, 1 H) 7.25 (d, J=8.08 Hz, 1 H) 8.85 (s, 1 H)

Sources & evidence

ORD record
ord-12c0c659b35848f28266dee47f8240ae
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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