Triethylamine → HCID 54096145, compound

HRID 374229Notes

Reaction equation

HRID 374229 reaction equation
Cl.[CH3:2][C:3]1[CH2:8][S:7][C:6]([NH:9][NH2:10])=[N:5][N:4]=1.C(N(CC)CC)C.[N+:18]([C:21]1[CH:43]=[CH:42][C:24]([O:25][CH:26]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:27](Cl)=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19]>C(#N)C.C(OCC)(=O)C>[N+:18]([C:21]1[CH:43]=[CH:42][C:24]([O:25][CH:26]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:27]([NH:10][NH:9][C:6]2[S:7][CH2:8][C:3]([CH3:2])=[N:4][N:5]=2)=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27351052-(4-nitrophenoxy)tetradecanoyl ChlorideHCID 178434113HCID 178434113, compound

Product 1

HCID 54096145HCID 54096145, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 24.25 g (0.134 m) of (5-methyl-6H-1,3,4-thiadiazin-2-yl)-hydrazine hydrochloride (2b) and 25.9 g (0.256 m) of triethylamine in 170 ml of acetonitrile is cooled to 0° C. A solution of 46.8 g (0.122 m) of 2-(4-nitrophenoxy)tetradecanoyl chloride (3b) in 50 ml of ethyl acetate is added slowly to the mixture keeping the temperature at 0-5° C. over an hour. The resulting mixture is stirred at 0° C. for 30 min, then warmed up to room temperature and stirred for another hour. After the reaction is complete, 170 ml of ethyl acetate is added and the mixture is stirred for 15 min. The solid is collected, washed with ethyl acetate, dried, and reslurried in 300 ml of water to remove triethylamine hydrochloride. The product is collected, washed with water, and dried to give 33.0 g (55%) of 2-(2-[4-nitrophenoxy] tetradecanoyl)-1-(5-methyl 6H-1, 3,4 thiadiazin-2-yl)hydrazine (1b) with 93 area % by HPLC.

Workup

  1. customat 0-5° C.
  2. customover an hour
  3. temperaturewarmed up to room temperature
  4. stirringstirred for another hour
  5. stirringthe mixture is stirred for 15 min
  6. customThe solid is collected
  7. washwashed with ethyl acetate
  8. customdried
  9. customto remove triethylamine hydrochloride
  10. customThe product is collected
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-66448e42a73e452cabd93cd5a0633c53
Source dataset
uspto-grants-1992_11
Patent number
US05166378

Reaction notes

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