Thiomorpholine 1-oxide → HCID 54161598, compound

HRID 1283459Notes

Reaction equation

HRID 1283459 reaction equation
[Cl:1][C:2]1[C:3](OC2C=CC=CC=2)=[N:4][C:5]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:6][C:7]=1[C:8]#[N:9].[NH:23]1[CH2:28][CH2:27][S:26](=[O:29])[CH2:25][CH2:24]1>O>[Cl:1][C:2]1[C:3]([N:23]2[CH2:28][CH2:27][S:26](=[O:29])[CH2:25][CH2:24]2)=[N:4][C:5]([N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[N:6][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 12600299Thiomorpholine 1-oxideHCID 21517877HCID 21517877, compound

Product 1

HCID 54161598HCID 54161598, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.3 gm (0.001 mol) of 5-chloro-6-cyano-4-phenoxy-2-piperazino-pyrimidine [m.p. 126°-128°C, obtained from 6-cyano-2,5-dichloro-4-phenoxy-pyrimidine and piperazine in acetone/dioxane (1:1) while cooling] were heated with 2.3 gm (0.02 mol) of thiomorpholine-1-oxide at about 140°C for 90 minutes. The dark colored molten mass was taken up in a small quantity of water, and the precipitated raw reaction product was purified on a silicagel column [eluant: methanol/concentrated ammonia (8:1)]. After reprecipitation from 0.2 N hydrochloric acid with ammonia, 5-chloro-6-cyano-2-piperazino-4-(1-oxido-thiomorpholino)-pyrimidine, m.p. 206°-208°C, was obtained.

Workup

  1. customthe precipitated raw
  2. customreaction product
  3. customwas purified on a silicagel column [eluant: methanol/concentrated ammonia (8:1)]
  4. customAfter reprecipitation from 0.2 N hydrochloric acid with ammonia, 5-chloro-6-cyano-2-piperazino-4-(1-oxido-thiomorpholino)-pyrimidine, m.p. 206°-208°C
  5. customwas obtained

Sources & evidence

ORD record
ord-cbb45b253a654f409d001de2be33ff20
Source dataset
uspto-grants-1976_08
Patent number
US03975384

Reaction notes

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