1-Hydroxybenzotriazole → HCID 54195013, compound

HRID 1977264Notes

Reaction equation

HRID 1977264 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:20][C:19]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)=[N:18][N:17]=2)=[CH:12][CH:11]=1.O[N:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[N:32]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[N:31]1([O:26][C:25](=[O:27])[C:24]2[CH:23]=[CH:22][C:21]([C:19]3[S:20][C:16]([C:13]4[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:15][CH:14]=4)=[N:17][N:18]=3)=[CH:29][CH:28]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[N:32]1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21997468HCID 21997468, compound

Product 1

HCID 54195013HCID 54195013, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[5-[4-(6-methoxy-n-hexyloxy)phenyl]-1,3,4-thiadiazole-2-yl]benzoic acid (50 g), 1-hydroxybenzotriazole (18 g) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide, hydrochloride (34.86 g) in methylene chloride (1 L) was stirred for 16 hours at room temperature then evaportated under reduced pressure and dried for 1 hour under hi-vacuum. Water (1 L) was added to the residue and the resulting precipitate collected by filtration, washed with water (1 L×5), acetonitrile (1L×5), isopropyl ether (250 ml×2), then dried under hi-vacuum to give 4-[5-[4-(6-methoxy-n-hexyloxy)phenyl]-1,3,4-thiadiazol-2-yl]benzoic acid benzotriazol-1-yl ester (56.92 g) as a yellow powder.

Workup

  1. customdried for 1 hour under hi-vacuum
  2. additionWater (1 L) was added to the residue
  3. filtrationthe resulting precipitate collected by filtration
  4. washwashed with water (1 L×5), acetonitrile (1L×5), isopropyl ether (250 ml×2)
  5. customdried under hi-vacuum

Sources & evidence

ORD record
ord-b6a7a6f084f1489c955af6928500adc9
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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