3-Chloropropionyl chloride → 1-(3-Chloropropanoyl)indoline-5-sulfonamide

HRID 528845Notes

Reaction equation

HRID 528845 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])CCCC[CH2:2]1.N1C2C(=CC(S(N)(=O)=O)=CC=2)CC1.[Cl:35]CCC(Cl)=O>>[Cl:35][CH2:2][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 693643-Chloropropionyl chlorideHCID 80272522,3-dihydro-1H-indole-5-sulfonamide2×HCID 606987421-(Cyclohexanecarbonyl)indoline-5-sulfonamide

Product 1

HCID 867188871-(3-Chloropropanoyl)indoline-5-sulfonamideYield 98%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 55, indoline-5-sulfonamide (Intermediate 54A, 300 mg, 1.51 mmol) and 3-chloropropanoyl chloride (189 μL, 1.97 mmol) were converted to the title compound (430 mg, 98%). 1H NMR (DMSO-d6) δ 8.16 (d, J=8.1 Hz, 1H), 7.66-7.63 (m, 2H), 7.22 (s, 2H), 4.18 (t, J=8.6 Hz, 2H), 3.89-3.86 (m, 2H), 3.21 (t, J=8.5 Hz, 2H), 3.03 (t, J=6.4 Hz, 2H); MS (ESI+) m/z 289.2 (M+H)+.

Sources & evidence

ORD record
ord-7dd8c9ffe5be4bacaa2a95906a3ad15b
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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