Triethylamine → Hydrochloric Acid

HRID 615360Notes

Reaction equation

HRID 615360 reaction equation
[Cl:1][C:2]([O:4][CH2:5][CH3:6])=[O:3].N[C:8]1[CH:17]=[CH:16][C:11]2[N:12]=[C:13]([SH:15])[S:14][C:10]=2[CH:9]=1.C([N:20](CC)CC)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[ClH:1].[CH2:5]([O:4][C:2]([NH:20][N:12]1[C:11]2[CH:16]=[CH:17][CH:8]=[CH:9][C:10]=2[S:14][CH:13]1[SH:15])=[O:3])[CH3:6]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178418618HCID 178418618, compound

Product 2

HCID 313Hydrochloric AcidHCID 86739914HCID 86739914, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl chloroformate (23.88 g, 0.22 mole) was added dropwise to a solution of 6-amino-2-mercaptobenzothiazole (18.23 g, 0.1 mole), triethylamine (22.26 g, 0.22 mole), 4-dimethylaminopyridine (100 mg) in N,N-dimethylformamide (100 ml) with stirring at 0° C. over a 1/2 hour period. The mixture was brought to ambient temperature then stirred for 2 hours. The reaction mixture was added to dilute aqueous hydrochloric acid-ice to precipitate a solid product. Reprecipitation by dissolution in aqueous sodium hydroxide solution then acidification with 12N HCl gave 17.50 g of 6-(N-ethoxycarbonylamino-2-mercaptobenzothiazole, m.p. 310°-312° C.

Workup

  1. customwas brought to ambient temperature
  2. stirringthen stirred for 2 hours
  3. customto precipitate a solid product
  4. customReprecipitation
  5. dissolutionby dissolution in aqueous sodium hydroxide solution

Sources & evidence

ORD record
ord-9aa82e3cccf7483087be12fceb51e2ed
Source dataset
uspto-grants-1985_02
Patent number
US04499103

Reaction notes

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