Water → HCID 9836534, compound

HRID 1375059Notes

Reaction equation

HRID 1375059 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[S:14]([NH2:17])(=[O:16])=[O:15].ClS([N:22]=[C:23]=[O:24])(=O)=O.O>C(Cl)Cl>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[S:4][C:3]([S:14]([NH2:17])(=[O:15])=[O:16])=[C:2]([NH:1][C:23]([NH2:22])=[O:24])[CH:6]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 58784945HCID 58784945, compound

Product 1

HCID 9836534HCID 9836534, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of 3c (30 mg, 0.11 mol) in CH2Cl2 (10 mL) was added chlorosulfonyl isocyanate (14 μL, 0.165 mmol). The resultant mixture was stirred at room temperature for 3 h, then mixed with water (0.5 mL). Separation using a reverse phase HPLC afforded 3d (20 mg, 58%) as a white solid: MS (ES) 316 (M+H)+; 1H NMR (400 MHz, CD3OD) δ8.02 (s, 1 H), 7.69 (m, 2 H), 7.20 (m, 2 H).

Workup

  1. customSeparation

Sources & evidence

ORD record
ord-db91fa01d4514ff2bde63d3043673b0f
Source dataset
uspto-grants-2007_01
Patent number
US07166639B2

Reaction notes

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