m-Chloroperbenzoic acid → HCID 178510681, compound

HRID 1355360Notes

Reaction equation

HRID 1355360 reaction equation
CS[C:3]1[N:4]=[N:5][C:6]([C:20]#[N:21])=[C:7]([N:9]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[CH2:11][CH2:10]2)[N:8]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[OH:30][C:3]1[N:4]=[N:5][C:6]([C:20]#[N:21])=[C:7]([N:9]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[CH2:11][CH2:10]2)[N:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18506776HCID 18506776, compound

Product 1

HCID 178510681HCID 178510681, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 200 mg (0.67 mmol) of 3-methylsulfanyl-5-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-[1,2,4]triazine-6-carbonitrile in 10 ml of dichloromethane was cooled to 0° C. and treated with 332 mg (1.35 mmol) of 3-chloro-perbenzoic acid (70%). The reaction mixture was warmed up to room temperature and stirred overnight. For the working-up, the reaction mixture was diluted with 10 ml of dichloromethane and extracted twice with 10 ml of a saturated solution of sodium hydrogencarbonate. The combined organic phases were dried over sodium sulfate, and evaporated under reduced pressure. The resulting residue, 170 mg of a yellow powder, was purified by chromatograhy on silica gel with a 98:2 mixture of dichloromethane and methanol as eluent. There were obtained 154 mg (86% of theory) of 3-hydroxy-5-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-[1,2,4]triazine-6-carbonitrile as a yellowish solid; MS: 266 (M−H).

Workup

  1. extractionextracted twice with 10 ml of a saturated solution of sodium hydrogencarbonate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe resulting residue, 170 mg of a yellow powder, was purified by chromatograhy on silica gel with a 98:2 mixture of dichloromethane and methanol as eluent

Sources & evidence

ORD record
ord-8075b946dfd44d26b394a422d90440de
Source dataset
uspto-grants-2003_07
Patent number
US06586422B2

Reaction notes

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