Cyanamide → 5-(Oxan-4-yl)-1,3-thiazol-2-amine

Reaction equation

[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]=O)[CH2:3][CH2:2]1.N1CCCC1.O.C1(C)C=CC([S:22](O)(=O)=O)=CC=1.[S].[N:28]#[C:29][NH2:30]>>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[S:22][C:29]([NH2:30])=[N:28][CH:8]=2)[CH2:3][CH2:2]1

Participants

Reactant 5

HCID 9864Cyanamide

HCID 31268Pyrrolidine

HCID 521998p-Toluenesulfonic acid monohydrate

HCID 5362487Sulfur

HCID 177509432-(Oxan-4-yl)acetaldehyde

Product 1

HCID 866190505-(Oxan-4-yl)-1,3-thiazol-2-amine

Procedure

A mixture of (tetrahydro-pyran-4-yl)-acetaldehyde (Pharmacore), pyrrolidine, p-toluenesulfonic acid monohydrate, sulfur and cyanamide were processed using the method described in Example 136A to obtain the title compound. MS (ESI+) m/z 185 (M+H)+.

Sources & evidence

ORD record: ord-c186569924024ea5916ec40a4266a856
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006275B2

Reaction notes

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