1,2-Dimethoxyethane → 5-Isothiocyanato-6-methyl-2-(pyridin-2-yl)-1,3-benzoxazole

HRID 1287666Notes

Reaction equation

[NH2:1][C:2]1[C:3]([CH3:17])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)=[N:7][C:6]=2[CH:16]=1.C(=O)([O-])[O-].[Ca+2].C(COC)OC.[C:29](Cl)(Cl)=[S:30]>O>[N:1]([C:2]1[C:3]([CH3:17])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)=[N:7][C:6]=2[CH:16]=1)=[C:29]=[S:30]

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of 5-amino-6-methyl-2-(2-pyridinyl)benzoxazole (8.7 g, 0.044 mole), calcium carbonate (4.44 g, 0.044 mole), glyme (150 ml) and water (50 ml) is cooled to 5° C in an ice-bath, and thiophosgene (5.11 g, 0.044 mole) is added. The mixture is stirred for 0.5 hour at 5° C and then allowed to warm to room temperature and stirred for about 16 hours. The precipitated material is collected, washed with water and crystallized from glyme/water (3:1) yielding 8.1 g of the title compound, melting point 192°-194° C.

Workup

temperatureto warm to room temperature
stirringstirred for about 16 hours
customThe precipitated material is collected
washwashed with water
customcrystallized from glyme/water (3:1)

Sources & evidence

ORD record: ord-8a45861c30874eb1ad35005036f5619e
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03985755

Reaction notes

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