Toluene → 7-Chloro-1'-[4-(methylsulfonyl)phenyl]spiro[2H-3,1-benzoxazine-2,4' piperidin]-4(1H)-one

HRID 329929Notes

Reaction equation

HRID 329929 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:18][C:19]1[CH:20]=[C:21]([NH2:28])[C:22](=[CH:26][CH:27]=1)[C:23](O)=[O:24].C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]2[C:23](=[O:24])[O:17][C:14]3([NH:28][C:21]=2[CH:20]=1)[CH2:15][CH2:16][N:11]([C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=1)[CH2:12][CH2:13]3

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 666462-Amino-4-chlorobenzoic acidHCID 141563991-(4-Methanesulfonylphenyl)piperidin-4-one

Product 1

HCID 150559087-Chloro-1'-[4-(methylsulfonyl)phenyl]spiro[2H-3,1-benzoxazine-2,4' piperidin]-4(1H)-oneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.82 g (0.023 mol) of the compound of (B), 4 g (0.023 mol) of 4-chloroanthranilic acid, 75 ml of toluene, and 0.1 of p-toluenesulfonic acid is stirred at reflux with the azeotropic removal of water for 5 hours. After cooling, the resulting precipitate is collected, and washed with cold toluene to give 8.8 g (94%) of title compound: m.p. 193°-194° C.; IR (KBr) 3350, 1695, and 1600 cm-1 ; NMR (DMSO-d6) δ 7.84-7.70 (m, 2H), 7.76 (d, 2H), 7.16 (d, 2H), 6.90-6.84 (m, 1H), 3.78-3.66 (m, 2H), 3.48-3.36 (m, 2H), 3.12 (s, 3H), 2.18-2.08 (m, 2H) and 1.96-1.82 (m, 2H); MS m/e 487 (M+1).

Workup

  1. temperatureAfter cooling
  2. customthe resulting precipitate is collected
  3. washwashed with cold toluene

Sources & evidence

ORD record
ord-a3656ca68789489792985799ee0158b8
Source dataset
uspto-grants-1990_01
Patent number
US04894374

Reaction notes

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