9H-xanthene-9-carbonyl chloride → HCID 54046607, compound
Reaction equation
[CH2:1]([C:4]1[O:8][C:7]([NH2:9])=[N:6][CH:5]=1)[CH2:2][CH3:3].[CH:10]1[C:23]2[CH:22]([C:24](Cl)=[O:25])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:15][C:14]=2[CH:13]=[CH:12][CH:11]=1>>[CH2:1]([C:4]1[O:8][C:7]([NH:9][C:24]([CH:22]2[C:23]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[O:15][C:16]3[C:21]2=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:25])=[N:6][CH:5]=1)[CH2:2][CH3:3]Participants
Procedure
The title compound, white solid, m.p. 203-205° C. and MS: m/e=334.1 (M+) was prepared in accordance with the general method of example 44a from 5-propyl-oxazol-2-ylamine [Ber. 95,2419(1962)] and 9-xanthene-carboxylic acid chloride. 66b) The 5-propyl-oxazol-2-ylamine used in the above reaction was obtained as follows: 21.8 g (0.132 mol) of 2-bromobutyraldehyde [Chem.Ber., 70,1898(1937)] was dissolved in 67.5 ml of a 4:3 mixture of DMF and water. Urea, 8.77 g (0.145 mol) was added with stirring. The clear colorless solution was stirred for 16 h at 105° C. The resulting light yellow solution is cooled to 0° C. and 10 ml of 45% Sodium hydroxide solution was added. The solution turns dark yellow (pH 12). 100 ml of brine is added and the solution is extracted five times with 100 ml of a 9:1 mixture of methylene chloride and methanol. The combined organic phases were concentrated to yield 15.62 g of a reddish brown oil which was purified by flash chromatography on silica gel with a 9:1 mixture of methylene chloride and methanol as eluent. One obtains 6.2 g (0.049 mol, 37%) of 5-5-propyl-oxazol-2-ylamine as a yellow oil which was directly used without further purification, MS: m/e=126.1 (M+).
Sources & evidence
- ORD record
- ord-a4fa482db93142ef80f7a51911e4fd81
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06803381B1
Reaction notes
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