Hydrochloric Acid → (4-Phenyl-1,3-thiazol-2-yl)methanol

HRID 1112729Notes

Reaction equation

HRID 1112729 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.C([O:14][CH2:15][C:16]([NH2:18])=[S:17])(=O)C.Cl>O1CCOCC1>[OH:14][CH2:15][C:16]1[S:17][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6259Phenacyl bromideHCID 11018908Carbamothioylmethyl acetate

Product 1

HCID 698895(4-Phenyl-1,3-thiazol-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Bromoacetophenone (39.9 g; 0.2 mole) and 2-acetoxythioacetamide (30 g; 0.225 mole) were dissolved in dioxan (150 ml). The mixture was stirred and heated on a steam bath for 15 minutes, yielding a mass of crystals. Aqueous 5N HCl (40 ml) was added and the heating continued for a further 30 minutes. The dioxan was evaporated under vacuum and the residue neutralised with aqueous Na2CO3 solution. The solid was collected, washed with water and dried. After recrystallisation from benzene the product weighed 33.5 g (87%) and had a m.p. of 88°-9° C.

Workup

  1. temperatureheated on a steam bath for 15 minutes
  2. customyielding a mass of crystals
  3. customThe dioxan was evaporated under vacuum
  4. customThe solid was collected
  5. washwashed with water
  6. customdried
  7. customAfter recrystallisation from benzene the product

Sources & evidence

ORD record
ord-c8180b7732ca44979b4b9e687dd2f680
Source dataset
uspto-grants-1978_10
Patent number
US04123529

Reaction notes

Loading…