1-Bromohexadecane → HCID 13041371, compound

HRID 1156096Notes

Reaction equation

HRID 1156096 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:13])[CH:3]=1.[CH2:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[CH2:9]([O:8][C:6](=[O:7])[C:5]1[CH:11]=[CH:12][C:2]([NH:1][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])=[CH:3][C:4]=1[F:13])[CH3:10]

Participants

6

Reactant 4

HCID 82131-BromohexadecaneHCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 10797532Ethyl 4-Amino-2-fluorobenzoate

Product 1

HCID 13041371HCID 13041371, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2.6 g of ethyl 4-amino-2-fluorobenzoate 4.5 g of hexadecylbromide, 2.0 g of anhydrous potassium carbonate and 20 ml of hexamethylphosphoramide is heated to 130° C. for 22 hours. The mixture is cooled, diluted with 200 ml of water, and extracted twice with ethyl ether. The combined extracts are washed with water, dried, and the ether evaporated and the residue upon recrystallization from hexane yields ethyl-2-fluoro-4-(hexadecylamino)benzoate as a white solid.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted twice with ethyl ether
  3. washThe combined extracts are washed with water
  4. customdried
  5. customthe ether evaporated
  6. customthe residue upon recrystallization from hexane

Sources & evidence

ORD record
ord-1fa72c2317a249cca9f198d49563e807
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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