Triethylamine → HCID 178527855, compound

HRID 2229161Notes

Reaction equation

HRID 2229161 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5].[C:13](Cl)(Cl)=[S:14].C(N(CC)CC)C>ClCCl.[OH-].[Na+].CO>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]2[O:5][C:13]([SH:14])=[N:2][CH:3]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 27982112-Amino-1-(4-chlorophenyl)ethan-1-one hydrochloride

Product 1

HCID 178527855HCID 178527855, compoundYield 14.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-amino-4′-chloroacetophenone hydrochloride (1.48 g) in 30 ml of dichloromethane were added 1.65 g of thiophosgene and 3.63 g of triethylamine at 0° C. and the mixture was stirred over night at room temperature. To the reaction mixture were added IN sodium hydroxide solution and methanol. The resulting mixture was stirred at room temperature and partitioned between ethyl acetate and water. The aqueous layer was neutralized by adding dil. hydrochloric acid and the resulting crystal was collected and dried to give 220 mg of 5-(4-chlorophenyl)-2-mercaptooxazole.

Workup

  1. stirringThe resulting mixture was stirred at room temperature
  2. custompartitioned between ethyl acetate and water
  3. additionby adding dil. hydrochloric acid
  4. customthe resulting crystal was collected
  5. customdried

Sources & evidence

ORD record
ord-0fbf6ab94f994833862094774af4b9cb
Source dataset
uspto-grants-2002_07
Patent number
US06420367B1

Reaction notes

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