Chloroacetyl chloride → 1-(2-chloroacetyl)-2,3-dihydro-1H-indole-5-sulfonamide

HRID 528841Notes

Reaction equation

HRID 528841 reaction equation
[CH:1]1([C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)=[O:8])CCCCC1.N1C2C(=CC(S(N)(=O)=O)=CC=2)CC1.[Cl:35]CC(Cl)=O>>[Cl:35][CH2:1][C:7]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)=[O:8]

Participants

4

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 80272522,3-dihydro-1H-indole-5-sulfonamide2×HCID 606987421-(Cyclohexanecarbonyl)indoline-5-sulfonamide

Product 1

HCID 162270611-(2-chloroacetyl)-2,3-dihydro-1H-indole-5-sulfonamideYield 23%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 55, indoline-5-sulfonamide (Intermediate 54A, 500 mg, 2.52 mmol) and 2-chloroacetyl chloride (221 μL, 2.77 mmol) were converted to the title compound (160 mg, 23%). 1H NMR (DMSO-d6) δ 8.13 (d, J=8.1 Hz, 1H), 7.68-7.66 (m, 2H), 7.24 (s, 2H), 4.58 (s, 2H), 4.20 (t, J=8.5 Hz, 2H), 3.24 (t, J=8.5 Hz, 2H); MS(ESI+) m/z 275.0 (M+H)+.

Sources & evidence

ORD record
ord-6f495f5cca954443b21bb745420de5aa
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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