Iodine → 5-tert-butyl-3-(2-((cis)-2,6-dimethylmorpholino)ethyl)thiazol-2(3H)-imine

HRID 78533

Reaction equation

[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.[NH2:8][CH2:9][CH2:10][N:11]1[CH2:16][C@H:15]([CH3:17])[O:14][C@H:13]([CH3:18])[CH2:12]1.[S-:19][C:20]#[N:21].[K+].II>>[C:2]([C:3]1[S:19][C:20](=[NH:21])[N:8]([CH2:9][CH2:10][N:11]2[CH2:16][C@@H:15]([CH3:17])[O:14][C@@H:13]([CH3:18])[CH2:12]2)[CH:4]=1)([CH3:7])([CH3:6])[CH3:1]

Participants

Reactant 4

HCID 807Iodine

HCID 763353,3-Dimethylbutanal

HCID 516872Potassium thiocyanate

HCID 71449682-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethan-1-amine

Product 1

HCID 686236405-tert-butyl-3-(2-((cis)-2,6-dimethylmorpholino)ethyl)thiazol-2(3H)-imine

Procedure

Commercially available 3,3-dimethylbutanal (Aldrich), 4-(2-aminoethyl)-cis-2,6-dimethylmorpholine (Oakwood), potassium thiocyanate (Aldrich) and iodine (EMD chemicals) were processed using the method described in Example 315A to afford the title compound. MS (ESI+) m/z 298 (M+H)+.

Sources & evidence

ORD record: ord-36fc5c9db0d84a059829a33d35f48c22
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841334B2

Linked notes

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