Triethylamine → HCID 57980811, compound

HRID 1867973Notes

Reaction equation

HRID 1867973 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[S:9][C:10]2[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:11]=2[N:12]=1)([CH3:4])([CH3:3])[CH3:2].[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C>CC(C)=O>[C:1]([O:5][C:6]([NH:7][C:8]1[S:9][C:10]2[CH:16]=[C:15]([O:17][S:24]([C:20]3[S:19][CH:23]=[CH:22][CH:21]=3)(=[O:26])=[O:25])[CH:14]=[CH:13][C:11]=2[N:12]=1)=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 57630251HCID 57630251, compound2×

Product 1

HCID 57980811HCID 57980811, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (6-hydroxybenzothiazol-2-yl)carbamic acid tert-butyl ester (intermediate 14) (527 mg, 1.979 mmol), 2-thiophenesulfonyl chloride (433 mg, 2.37 mmol) and triethylamine (677 μl, 4.75 mmol) in 10 ml of acetone is stirred overnight at room temperature. The reaction medium is concentrated to dryness. The residue obtained is washed with water, with acetone and then with ethyl ether to give 621 mg of thiophene-2-sulfonic acid 2-tert-butoxycarbonylaminobenzothiazol-6-yl ester (light gray powder) in a yield of 76%.

Workup

  1. concentrationThe reaction medium is concentrated to dryness
  2. customThe residue obtained
  3. washis washed with water, with acetone

Sources & evidence

ORD record
ord-454489fc283a4bf8b2d268311efdb7cd
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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