Water → HCID 13268206, compound

HRID 1903381Notes

Reaction equation

HRID 1903381 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5](Cl)=[O:6].[NH2:14][C:15]1[S:16][CH2:17][C:18]([C:21]([CH2:25][CH3:26])([CH3:24])[CH2:22][CH3:23])=[N:19][N:20]=1.O>ClCCl.N1C=CC=CC=1>[CH2:22]([C:21]([C:18]1[CH2:17][S:16][C:15]([NH:14][C:5](=[O:6])[C:4]2[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[CH:9][C:8]=2[O:12][CH3:13])=[N:20][N:19]=1)([CH3:24])[CH2:25][CH3:26])[CH3:23]

Participants

6

Reactant 3

HCID 962WaterHCID 748102,6-Dimethoxybenzoyl chlorideHCID 132682045-(3-Methylpentan-3-yl)-6H-1,3,4-thiadiazin-2-amine

Product 1

HCID 13268206HCID 13268206, compoundYield 4.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Two grams of 2,6-dimethoxybenzoyl chloride dissolved in about 3 ml dichloromethane was added dropwise to a stirring solution of 1.99 g of 2-amino-5-(1-ethyl-1-methylpropyl)-6H-1,3,4-thiadiazine in 10 ml of pyridine. The mixture was stirred at room temperature for approximately 72 hours and poured into water. The product was extracted into ether and washed with water. The ether phase was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The resulting oil was chromatographed over silica gel eluting with a 1:4 (v:v) mixture of ethyl acetate/toluene. Fractions containing the major component were combined and the solvent was evaporated therefrom to afford 0.15 g of N-[5-(1-ethyl-1-methylpropyl)-6H-1,3,4-thiadiazin-2-yl]-2,6-dimethoxybenzamide. mp=134°-140° C.

Workup

  1. extractionThe product was extracted into ether
  2. washwashed with water
  3. dry with materialThe ether phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting oil was chromatographed over silica gel eluting with a 1:4 (v:v) mixture of ethyl acetate/toluene
  7. additionFractions containing the major component
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-171140e987c74216ad24763709204d0c
Source dataset
uspto-grants-1984_03
Patent number
US04436549

Reaction notes

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