m-Chloroperbenzoic acid → 2,8-Dimethyl-1-thia-3,8-diaza-spiro[4.5]dec-2-ene 8-oxide

HRID 1825849Notes

Reaction equation

HRID 1825849 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[S:17][C:16]2([CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)[CH2:15][N:14]=1.[O-2].[Al+3].[O-2].[O-2].[Al+3]>ClCCl>[CH3:12][C:13]1[S:17][C:16]2([CH2:22][CH2:21][N+:20]([O-:9])([CH3:23])[CH2:19][CH2:18]2)[CH2:15][N:14]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 9989226AluminaHCID 101764151-Methylpiperidine-4-spiro-(2'-methylthiazoline)

Product 1

HCID 221396412,8-Dimethyl-1-thia-3,8-diaza-spiro[4.5]dec-2-ene 8-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid, mCPBA, (1.40 gr, 8.11 mmol) in dichloromethane (30 ml) was added gradually to a solution of AF150(S) (1.45 gr, 7.88 mmol) in dichloromethane (10 ml). The reaction was stirred at room temperature overnight. Chromatography of the reaction mixture was on a column of natural aluminum oxide (Merck)(metanol:chloroform 1/49) gave AF406 (0.75 gr) as a crystalline solid. A sample was crystallized from ethylacetate. A very hygroscopic solid was obtained. mp. 130–132° C. (145–159° C. dec.); 1H NMR (300 MHz, CDCl3) δ 1.89 (m, 2H), 2.2 (t, j=1.5 Hz, CH3C═N), 2.82 (m, 2H), 3.24 (m, 2H), 3.25 (s, CH3N+O−), 3.35 (m, 2H), 4.03 (q, j=1.5 Hz, CH2N═C) ppm; IR(CHCl3) 2947, 1636, 1448, 1153, 931, 664 cm−1; MS(EI) 200 (M+), 184, 182, 149, 141, 140, 126, 110, 109, 108, 96, 82, 70.

Workup

  1. customgave AF406 (0.75 gr) as a crystalline solid
  2. customA sample was crystallized from ethylacetate
  3. customA very hygroscopic solid was obtained

Sources & evidence

ORD record
ord-7326ebff2f54449ea885829dda03867f
Source dataset
uspto-grants-2006_05
Patent number
US07049321B2

Reaction notes

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