2-Amino-5-Nitrothiazole → HCID 3113444, compound

HRID 1701832Notes

Reaction equation

HRID 1701832 reaction equation
[C:1]1([CH3:10])[C:2]([C:7](Cl)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:11][C:12]1[S:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][N:16]=1>N1C=CC=CC=1>[CH3:10][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:11][C:12]1[S:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][N:16]=1)=[O:8]

Participants

4

Reactant 2

HCID 84862-Amino-5-NitrothiazoleHCID 702762-Methylbenzoyl chloride

Product 1

HCID 3113444HCID 3113444, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of o-toluoyl chloride (17 g) in a few milliliters of pyridine was added dropwise to a suspension of 2-amino-5-nitrothiazole (16 g) in pyridine (100 ml), initially at room temperature, then at 0°. After the addition was complete, the reaction mixture was stirred for 2 hr at room temperature, and was then quenched in ice-water. Recrystallisation of the precipitated amide from 2-methoxyethanol afforded 2-methyl-N-(5-nitro-2-thiazolyl)benzamide, m.pt. 228°-230°.

Workup

  1. customat 0°
  2. additionAfter the addition
  3. customwas then quenched in ice-water
  4. customRecrystallisation of the precipitated amide from 2-methoxyethanol

Sources & evidence

ORD record
ord-7ed93acf481c4c1c90305a71463f7128
Source dataset
uspto-grants-1983_04
Patent number
US04379156

Reaction notes

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