Triethylamine → HCID 21543983, compound

HRID 1606611Notes

Reaction equation

HRID 1606611 reaction equation
Cl([O-])(=O)(=O)=[O:2].[C:6]([N+:10]1[O:11][C:12]([CH3:15])=[CH:13][CH:14]=1)([CH3:9])([CH3:8])[CH3:7].[CH2:16]([NH:22][C:23]1[CH:31]=[C:30]([Cl:32])[C:29]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][C:24]=1[C:25](O)=[O:26])[C:17]1[O:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>CN(C)C=O.O>[C:6]([NH:10][C:14](=[O:2])/[CH:13]=[C:12](\[O:11][C:25](=[O:26])[C:24]1[CH:28]=[C:29]([S:33]([CH3:36])(=[O:35])=[O:34])[C:30]([Cl:32])=[CH:31][C:23]=1[NH:22][CH2:16][C:17]1[O:21][CH:20]=[CH:19][CH:18]=1)/[CH3:15])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 151520Isoxazolium, 2-(1,1-dimethylethyl)-5-methyl-, perchlorate (1:1)HCID 21543990HCID 21543990, compound

Product 1

HCID 21543983HCID 21543983, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-tert-butyl-5-methylisoxazolium perchlorate (120 g.; 0.005 mole) is added to a solution of 2-furfurylamino-4-chloro-5-methylsulfonylbenzoic acid (1.65 g.; 0.005 mole) and triethylamine (0.7 ml.) in dimethylformamide (15 ml.). The resulting solution is allowed to stir at room temperature for 2 hours, and then diluted with H2O (75 ml.). The white solid which precipitates is collected and dried, yield 2.4 g. (crude), m.p. 140°-145° C. Recrystallization from butyl chloride yields N-tert-butyl-3-(2-furfurylamino-4-chloro-5-methylsulfonylbenzoyloxy)crotonamide, m.p. 148.5°-150° C. (dec. with eff.).

Workup

  1. customThe white solid which precipitates
  2. customis collected
  3. customdried
  4. customRecrystallization from butyl chloride

Sources & evidence

ORD record
ord-8786dac8b5f542c69a25bea4a301318c
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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