m-Chloroperbenzoic acid → HCID 21997628, compound

HRID 1977110Notes

Reaction equation

HRID 1977110 reaction equation
[C:1]1([C:7]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[S:9][C:8]=2[C:17]#[N:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:27])C=1>ClCCl>[C:1]1([C:7]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[S:9](=[O:27])[C:8]=2[C:17]#[N:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 125094783-Phenyl-4H-1,4-benzothiazine-2-carbonitrile

Product 1

HCID 21997628HCID 21997628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-phenyl-4H-1,4-benzothiazine-2-carbonitrile (0.10 g) and 3-chloroperbenzoic acid (0.17 g, purity 80%) in dichloromethane (8 ml) was stirred at 0° C. for 30 min. The mixture was filtered and the filter cake was washed with dichloromethane and dried to give the title compound as pale crystals. Yield 66 mg; mp 182-184° C.; 1H-nmr(DMSO) δ (ppm): 12.31 (br, 1H), 8.09-7.99 (m, 1H), 7.83-7.60 (m, 7H), 7.60-7.48 (m, 1H); IR(KBr) ν (cm−1): 3211, 3161, 2985, 2935, 2850, 2193 (C≡N ), 1603, 1548, 1502, 1463, 1429, 1004, 771, 703; MS m/e (rel. intensity): 250 (86%; M+−16), 249 (87%), 218 (39%), 211 (100%), 190 (11%), 146 (23%), 108 (43%), 69 (43%).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with dichloromethane
  3. customdried

Sources & evidence

ORD record
ord-170264b9304a4bcb9d116a91c1d179b0
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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