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Ammonium Chloride → 4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl methanesulfonate

HRID 2281071
Notes
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Reaction equation

HRID 2281071 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=1.C(N(CC)C(C)C)(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34].[Cl-].[NH4+]>ClCCl>[CH3:32][S:33]([O:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:3]2[CH:4]=[CH:5][C:6]3[N:7]([CH2:11][CH:12]4[CH2:14][CH2:13]4)[N:8]=[N:9][C:10]=3[C:2]=2[Cl:1])=[CH:20][CH:19]=1)(=[O:35])=[O:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chloride2×HCID 81531DiisopropylethylamineHCID 70977671HCID 70977671, compound

Product 1

HCID 867119864-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
0 °C

Procedure

{4-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]phenyl}methanol (0.71, 2.3 mmol) was dissolved in dichloromethane (7 mL) and treated with N,N-diisopropylethylamine (0.79 mL, 4.5 mmol). The mixture was cooled to 0° C. and treated with methanesulfonyl chloride (0.21 mL, 2.7 mmol) and after 1 hour, the mixture was treated with additional methanesulfonyl chloride (50 uL). After stirring for an additional 30 minutes, the mixture was poured into ammonium chloride (50 mL, aqueous saturated) and extracted with dichloromethane (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

  1. extractionextracted with dichloromethane (2×100 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe2047b710f14786a278a7737fce61d6
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139576B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes