Ethyl orthoformate → HCID 54081328, compound

HRID 2255485Notes

Reaction equation

HRID 2255485 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[N:7]=1.[CH:20](OCC)(OCC)[O:21][CH2:22][CH3:23]>>[CH:14]1([C:11]2[CH:12]=[CH:13][C:8]([C:6]3[N:7]=[C:3]([N:2]=[CH:20][O:21][CH2:22][CH3:23])[S:4][CH:5]=3)=[CH:9][CH:10]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 19738249HCID 19738249, compound

Product 1

HCID 54081328HCID 54081328, compoundYield 95.6%

Conditions

Temperature
130 °C

Procedure

A mixture of 2-amino-4-(4-cyclohexylphenyl)thiazole hydrochloride (1.0 g) and triethyl orthoformate (5 ml) was stirred at 130° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and to the remaining crystals was added hexane, followed by filtration. The filtrate was concentrated to give crystals of 4-(4-cyclohexylphenyl)-2-ethoxymethyleneaminothiazole (1.02 g, yield of 95.6 %). Recrystallization from diethyl etherhexane produced yellowish prisms, mp of 84° to 85° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the remaining crystals was added hexane
  3. filtrationfollowed by filtration
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b429b4a07c1f486b9ca69eb3a7f1d078
Source dataset
uspto-grants-1993_08
Patent number
US05240950

Reaction notes

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