Phenacyl bromide → HCID 22758602, compound

HRID 1704716Notes

Reaction equation

HRID 1704716 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[CH2:11]([N:18]1[CH2:23][NH:22][C:21](=[S:24])[NH:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O>[CH2:11]([N:18]1[CH2:23][N:22]2[C:2]([OH:3])([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:1][S:24][C:21]2=[N:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 6748065-benzyl-1,3,5-triazinane-2-thione

Product 1

HCID 22758602HCID 22758602, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5.0 grams (0.025 moles) of phenacyl bromide in 40 milliliters of acetone was mixed with a solution of 5.2 grams (0.025 moles) of 5-benzyl-3,4,5,6-tetrahydro-s-triazine-2(1H)-thione in 1200 milliliters of the same solvent and left for 2 hours at room temperature. The solution was then concentrated to 300 milliliters and left overnight. 3-Benzyl-6-hydroxy-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a]-s-triazine hydrobromide acetonate crystallized as a pale brown solid, m.p. 97°-99° C. The yield was 9.5 grams (82%).

Workup

  1. concentrationThe solution was then concentrated to 300 milliliters
  2. waitleft overnight
  3. custom3-Benzyl-6-hydroxy-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a]-s-triazine hydrobromide acetonate crystallized as a pale brown solid, m.p. 97°-99° C

Sources & evidence

ORD record
ord-802d56f8e1774649a53b49230d3b7e45
Source dataset
uspto-grants-1978_11
Patent number
US04127660

Reaction notes

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