Triethylamine → Methyl 4-amino-3-phenyl-1,2-thiazole-5-carboxylate

HRID 1506510Notes

Reaction equation

HRID 1506510 reaction equation
C(N(CC)CC)C.S(O/[N:19]=[C:20](\[C:27]#[N:28])/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(C1C=CC(C)=CC=1)(=O)=O.[SH:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]>CO>[NH2:28][C:27]1[C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:19][S:29][C:30]=1[C:31]([O:33][CH3:34])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 9554926Benzeneacetonitrile, alpha-[[[(4-methylphenyl)sulfonyl]oxy]imino]-

Product 1

HCID 13073192Methyl 4-amino-3-phenyl-1,2-thiazole-5-carboxylateYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (5.39 g, 53.3 mmol) was added dropwise to a stirred solution of (Z)—N-(tosyloxy)benzimidoyl cyanide (Preparation 103B, 8 g, 26.6 mmol) and methyl 2-mercaptoacetate (2.86 mL, 32.0 mmol) in MeOH (70 mL) at room temperature. After stirring at room temperature for 3 h, the reaction was cooled and treated with 100 mL ice/water. The resultant solid was filtered and washed with water. The solid was vacuum dried to yield 6 g brown colored solid. Recrystallization from hexane/ethyl acetate yielded the titled compound (3 g) as a beige colored needles. The compound had an LC/MS M+1=235.2.

Workup

  1. temperaturethe reaction was cooled
  2. filtrationThe resultant solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0c5e2b29e0404a1eaaa7188a187c292e
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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